- Ultrasound promoted bromination of activated arenes with N-bromosuccinimide
-
Ultrasound irradiation has resulted in the selective monobromination of activated aromatics with N-Bromosuccinimide (NBS) in carbon tetrachloride at ambient conditions in the absence of any added catalyst.
- Paul,Sudalai,Daniel,Srinivasan
-
-
Read Online
- Synthesis of Flubromazepam Positional Isomers for Forensic Analysis
-
Designer benzodiazepines have recently appeared in many forensic cases as legal alternatives to federally scheduled drugs such as diazepam (Valium) and alprazolam (Xanax). Though current forensic instrumental techniques are often sufficient for identifying novel psychoactive substances, they may not readily differentiate between potential positional isomers. Additionally, characterization data for positional isomers of known designer benzodiazepines are widely nonexistent. In this study, flubromazepam, a recognized designer benzodiazepine since 2012, was targeted for synthesis and characterization due to its potential for federal scheduling and current legal status within the United States. A practical synthetic method was developed to prepare purified reference materials for each positional isomer of flubromazepam in which the positions of the bromine and fluorine substituents were varied. Possible isomers (9 of the 12) were successfully prepared and used for further analysis.
- Allred, B. McKay,France, Stefan,Jones, Lonnie V.,Ligon, Evelyn S.,Nawyn, Jason,Reinhardt, Daniel V.
-
-
Read Online
- Use of 1-halo derivatives of the 2,2,6,6-tetramethylpiperidine series as oxidants and halogenating agents
-
1-Halo derivatives of the 2,2,6,6-tetramethylpiperidine series oxidize sterically hindered phenols to form dimers and p-quinones.
- Kashparova,Kagan,Zhukova,Ivakhnenko
-
-
Read Online
- Bromodecarbonylation and bromodecarboxylation of electron-rich benzaldehydes and benzoic acids with oxone and sodium bromide
-
Benzaldehydes and benzoic acids bearing ortho- and paraelectron donating substituents having unshared electron-pair have undergone bromodecarbonylation or bromodecarboxylation on treatment with sodium bromide in the presence of Oxone in aqueous methanol.
- Koo, Bon-Suk,Kim, Eun-Hoo,Lee, Kee-Jung
-
-
Read Online
- Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
-
A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).
- Zhang, Xinglu,Liu, Zhiqiang,Gao, Yu,Li, Feng,Tian, Yaming,Li, Chunju,Jia, Xueshun,Li, Jian
-
-
Read Online
- Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine
-
A regioselective and highly efficient method for bromination of aromatic compounds in the presence of a stoichiometric amount of hexamethylenetetramine- bromine (HMTAB) as an efficient reagent in dichloromethane is reported. The selectivity depends on the temperature and nature of the substituent on the substrate. The reactivity of this reagent was increased by supporting it to silica gel for bromination of less activated compounds.
- Heravi, Majid M.,Abdolhosseini, Nafiseh,Oskooie, Hossein A.
-
-
Read Online
- Liquid phase regioselective bromination of aromatic compounds over HZSM-5 catalyst
-
A simple, efficient, regioselective and environmentally safe method for oxybromination of activated aromatics catalyzed by HZSM-5 is reported. The electrophilic substitution of bromine generated from KBr using HZSM-5 as a catalyst and H2O2 as an oxidant.
- Narender,Srinivasu,Kulkarni,Raghavan
-
-
Read Online
- Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
-
Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
- Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
-
-
Read Online
- Selectivity enhancement of aromatic halogenation reactions at the micellar interface: Effect of highly ionic media
-
Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.
- Samant, Bhupesh S.,Bhagwat, Sunil S.
-
-
Read Online
- A new mild and selective reagent for nuclear bromination
-
Hexamethylene tetramine tribromide HMTAHBr3 - a new, mild and regioselective brominant is reported for bromination of aromatic hydrocarbons, substituted ethers, phenols and anilides in high yields.
- Bisarya,Rao
-
-
Read Online
- Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds
-
In this study, a new method of synthesis of polyethylene glycol supported potassium tribromide (PEG KBr3) and its application in acylation and bromination reactions are reported. Ammonium persulphate oxidizes KBr to the corresponding tribromide which is entrapped by polyethylene glycol leading to stable PEG KBr3. The reagent is proved to be highly efficient for the acylation of variety of alcohols and bromination of activated aromatic substrates. The method is a mild, one pot reaction and involves no use of toxic reagents.
- Dey, Rupa Rani,Dhar, Siddhartha Sankar
-
-
Read Online
- Regioselective synthesis of para-bromo aromatic compounds
-
Reaction of substituted benzenerings with N-bromophthalimide, underneutral conditions, gave the corresponding bromo derivatives with a preference for the formation of the para bromoisomer over the ortho isomer. The sim pie work-up procedure minimizes loss of product and the yields are good.
- Khazaei, Ardeshir,Manesh, Abbas Amini,Safi, Vahid Reza
-
-
Read Online
- 4,4-Dibromo-3-methylpyrazol-5-one: New applications for selective monobromination of phenols and oxidation of sulfides to sulfoxides
-
Dibromopyrazolone 1, a stable, crystalline solid effects para selective monobromination of phenols and aniline substrates under mild conditions. Selective oxidation of sulfides to sulfoxides can also be accomplished by using 1 in high yields.
- Mashraqui, Sabir H.,Mudaliar, Chandrashekar D.,Hariharasubrahmanian, Harini
-
-
Read Online
- Oxidation of benzyl alcohols with Oxone and sodium bromide
-
Reaction of benzyl alcohols with Oxone and sodium bromide in aqueous acetonitrile gave the corresponding benzaldehydes in excellent yields. However, electron-rich benzyl alcohols afforded ring bromination products via bromodecarbonylation of the resulting benzaldehydes.
- Koo, Bon-Suk,Lee, Chang Keun,Lee, Kee-Jung
-
-
Read Online
- A new method for the oxybromination of aromatic compounds with copper(II)bromide and potassium dichromate
-
A new and mild method for oxybromination of aromatic compounds with CuBr2 and K2Cr2O7 in HOAC is reported. Copyright Taylor & Francis Inc.
- Badri, Rashid,Shushizadeh, Mohammad Reza
-
-
Read Online
- Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
-
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
- Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
-
-
Read Online
- In(OTf)3-Catalyzed Synthesis of 2,3-Dihydro-1 H-benzo[ e]indoles and 2,3-Dihydrobenzofurans via [3 + 2] Annulation
-
An In(OTf)3-catalyzed intermolecular [3 + 2] annulation for the synthesis of 2,3-dihydro-1H-benzo[e]indoles and 2,3-dihydrobenzofurans from readily available substrates has been achieved. This approach takes advantage of oxetane and para-quinone methide as important functional units in the key intermediate. β-Naphthylamines and phenols have been demonstrated as excellent reaction partners.
- Liu, Shuxuan,Zang, Yu,Huang, Hai,Sun, Jianwei
-
-
Read Online
- Sono-bromination of aromatic compounds based on the ultrasonic advanced oxidation processes
-
A novel, mild "sono-halogenation" of various aromatic compounds with potassium halide was investigated under ultrasound in a biphasic carbon tetrachloride/water medium. The feasibility study was first undertaken with the potassium bromide and then extended to chloride and iodide analogues. This methodology could be considered as a new expansion of the ultrasonic advanced oxidation processes (UAOPs) into a synthetic aspect as the developed methodology is linked to the sonolytic disappearance of carbon tetrachloride. Advantages of the present method are not only that the manipulation of the bromination is simple and green, but also that the halogenating agents used are readily available, inexpensive, and easy-handling.
- Fujita, Mitsue,Lévêque, Jean-Marc,Komatsu, Naoki,Kimura, Takahide
-
-
Read Online
- Green synthesis of tetraalkylammonium tribromide using cerium(IV) ammonium nitrate (CAN) as oxidant
-
Cerium(IV) ammonium nitrate (CAN) mediates oxidation of tetraalkylammonium bromide to tetraalkylammonium tribromide in greener reaction conditions using water as solvent. The procedure is simple, convenient, and environmentally benign for the synthesis of tetraalkylammonium tribromide with great yields. Copyright Taylor & Francis Group, LLC.
- Borah, Ruli,Thakur, Ashim Jyoti
-
-
Read Online
- A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions
-
Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.
- Adibi, Hadi,Hajipour, Abdol R.,Hashemi, Majid
-
-
Read Online
- Desulfurization of Thioamides into Amides with H2O 2/ZrCl4 Reagent System
-
The hydrogen peroxide/zirconium(IV) chloride reagent system has been used as a new and efficient reagent for the deprotection/desulfurization of thioamides to amides. This system is reasonably general and can be applied to the conversion of several thioamides to the corresponding amides. The salient features of this protocol are short reaction times, good chemoselectivity, cleaner reaction profiles, and simple workup that precludes the use of toxic solvents. Georg Thieme Verlag Stuttgart.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Tirandaz, Yeganeh
-
-
Read Online
- Regioselective one-pot bromination of aromatic amines
-
(Matrix Presented) Treatment of aniline with n-butyllithium and then trimethyltin chloride gave the tin amide (PhNH-SnMe3) in situ. Without isolation of the tin amide reaction with bromine and workup with aqueous fluoride ion gave p-bromoaniline in 76% yield, with no dibromoaniline or o-bromoaniline. Application of this sequence to 11 different aromatic amines gave selective bromination in 36-91% yields, without formation of dibromides. This constitutes a good general method for the regioselective bromination of aromatic amines.
- Smith, Michael B.,Guo, Lisa,Okeyo, Sherrad,Stenzel, Jason,Yanella, James,LaChapelle, Eric
-
-
Read Online
- An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and oxone
-
A simple, efficient and regioselective method for oxybromination of aromatics is reported. The electrophilic substitution of bromine generated in situ from potassium bromide using oxone as an oxidant for the first time.
- Narender,Srinivasu,Ramakrishna Prasad,Kulkarni,Raghavan
-
-
Read Online
- Regioselective and efficient bromination of anilides on water using HBr and Selectfluor
-
A metal-, additive-, and Br2-free highly regioselective bromination of anilides using HBr and Selectfluor is presented. This reaction proceeded under mild conditions with high efficiency and good functional group tolerance, and water served as the solvent. In general, with substrates bearing no para-substituent, para-mono-bromination occurred exclusively, while ortho-mono-brominated anilides were the only products when para-positions were blocked. The incorporation of a stronger orienting group might result in a reversed regioselectivity, and the reaction was sensitive to steric hindrance.
- Liang, Deqiang,Li, Xiangguang,Wang, Chaowu,Dong, Qishan,Wang, Baoling,Wang, Hai
-
-
Read Online
- Peroxo–tungstate(VI) complexes: syntheses, characterization, reactivity, and DFT studies
-
Abstract: Three new oxodiperoxo–tungsten(VI) complexes containing benzene core carboxylic acids, viz., benzoic acid, 2-chlorobenzoic acid, and 3-aminobenzoic acid as co-ligands have been synthesized from reaction of Na2WO6H4, 30% H2O2 and the corresponding co-ligands in aqueous medium. The compounds have been comprehensively characterized by elemental analyses, FT-IR, 1H NMR, UV–Vis spectral studies as well as by mass spectrometric and TGA analyses. The infrared spectra suggest occurrence of terminally bonded W=O as well as triangular bidentate peroxo groups (C2v) and monodentate carboxylate group bound to the WO4+ center. The mass spectra of the compounds are in good agreement with proposed molecular formulations. Thermogravimetric analyses indicate the existence of both lattice and coordinated water molecules in the complexes. Density functional theory (DFT) calculations were used to compute the frequencies of relevant vibrational modes, electronic properties and also to investigate structure of the compounds. Compound potassium(aquo)(2-chlorobenzoato)oxodiperoxo–tungstate(VI)dihydrate acts as an oxidant for bromide ion in aqueous phase bromination of chosen organic substrates to their corresponding bromo-organics. Graphical abstract: [Figure not available: see fulltext.]
- Das, Nandita,Chowdhury, Shubhamoy,Purkayastha, Ranendra N. Dutta
-
-
Read Online
- Regioselective control of aromatic halogenation reactions in carbon nanotube nanoreactors
-
The use of single-walled carbon nanotubes as effective nanoreactors for preparative chemical reactions has been demonstrated for the first time. Extreme spatial confinement of reactant molecules inside nanotubes has been shown to drastically affect both the regioselectivity and kinetics of aromatic halogenation reactions.
- Miners, Scott A.,Rance, Graham A.,Khlobystov, Andrei N.
-
-
Read Online
- Bromine formation in solid NaBr/KNO3 mixture and assay of this reaction via bromination of activated aromatics
-
Bromine formation in the mixture of solid NaBr and KNO3 was observed and the process was studied in different acidified organic solvent–water mixtures by monitoring the bromination of acetanilide and other compounds, containing activated aromatic substituents. This assay is based on fast bromination reaction of these aromatic compounds, as differently from the assay of Br2, the brominated aromatics can be easily determined by conventional gas chromatography–mass spectrometry (GC–MS) methods. It was found that bromine was generated autocatalytically on the surface of salt crystals and the reaction was characterized by a lag period, the duration of which depended on reaction conditions, and importantly on the type of the organic solvent in the reaction mixture. As the bromine formation could be easily controlled by reaction conditions, it was suggested that the studied reaction might have practical applications as an environmentally friendly and economically feasible bromination method. It was also shown that the bromination of aromatics followed the mechanism of classical electrophilic aromatic substitution reaction.
- Rahu, Ida,Keki?ev, Ott,J?rv, Jaak,Burk, Peeter
-
-
Read Online
- An efficient chemo and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate
-
A mild, efficient and highly chemo- and regioselective method for the bromination of electron rich aromatic molecules has been developed by electrophilic substitution of Br+, which was generated in situ from LiBr using ceric ammonium nitrate as the oxidant. Free aromatic amines remained unaffected under the reaction conditions.
- Roy, Subhas Chandra,Guin, Chandrani,Rana, Kalyan Kumar,Maiti, Gourhari
-
-
Read Online
- Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
-
(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
- Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
-
-
Read Online
- BROMINATION OF AROMATIC MOLECULES WITH POLYMER SUPPORTED REAGENTS
-
Crosslinked co poly/styrene-4-vinyl(N-hexylpyridinium bromide) was converted with bromine or chlorine to insoluble polymer supported complexes 1 or 2 respectively, and their reactivity studied in reactions with various aromatic molecules.Reagent 1 was found in all cases to be milder than reagent 2 and regiospecifically transformed alkoxy and amino substituted benzenes (3) into 4-bromo derivatives, while corresponding reactions with 2 resulted in dibromo derivatives.Several benzoheterocyclic molecules were converted with 1 to substitution or addition products, i.e. 2,3-dibromo-N-methylpyrrole, 3-bromobenzo/b/thiophene, and 2,3-dibromo-2,3-dihydrobenzofuran.In the series of ortho-alkyl disubstituted benzene derivatives, i.e. o-xylene, indane, and tetraline, where the Mills-Nixon effect was established with various electrophilic reagents, bromination reactions with 2 showed higher β-selectivity than the corresponding reactions with bromine.The rate of bromination in various alkyl substituted benzenes with reagent 2 depended on the magnitude of the alkyl group, as well as the para/ortho regioselectivity, amounting to 100percent in the case of tert-butylbenzene.
- Zajc, Barbara,Zupan, Marko
-
-
Read Online
- Determination of the Rate Constant of Bromination of Acetanilide with the Technique of the Diffusion Layer Titration on the Rotating Ring-Disc Elektrode
-
The kinetics of the bromination of acetanilide has been studied with the diffusion layer titration method.The results have been obtained using the apparatus which consists of the ring-disc electrode and an amperostatpotentiostat system.Dependence of the ring current on the disc current has been determined as a function of rotation speeds of the electrode, of the solution concentration and temperature.It has been shown the bromination reaction of acetanilide exhibits by first order kinetics.In that case Br2 and Br3- are the brominating species.The rate of bromination changes with the concentration of the Br- ions.This reaction rate depends on reactions of molecular bromine with acetanilide.For 0.033 ->-1s-1 -1 s-1 (+> = 1.34; T = 298). - Keywords: Acetanilide; Bromination; Kinetics
- Basak, Joanna,Sykut, Kazimierz
-
-
Read Online
- Novel bromination method for anilines and anisoles using NH 4Br/H2O2 in CH3COOH
-
A simple, efficient, regioselective, environmentally safe, and economical method for the oxybromination of anilines and anisoles without catalyst is reported. The electrophilic substitution of bromine generated in situ from ammonium bromide as a bromine source and hydrogen peroxide as an oxidant for the first time.
- Krishna Mohan,Narender,Srinivasu,Kulkarni,Raghavan
-
-
Read Online
- Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)
-
In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase. Taylor &Francis Group, LLC.
- Chattopadhyay, Gautam,Ray, Partha Sinha
-
-
Read Online
- Silica-supported quinolinium tribromide: A recoverable solid brominating reagent for regioselective monobromination of aromatic amines
-
Silica-supported quinolinium tribromide was synthesized and found to be an efficient, stable, and recoverable solid brominating reagent for the regioselective monobromination of aromatic amines. This protocol has advantages of high yield, mild condition and simple work-up procedure.
- Li, Zheng,Sun, Xiunan,Wang, Lue,Li, Yanbo,Ma, Yuanhong
-
-
Read Online
- Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide
-
Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.
- Bovonsombat, Pakorn,Teecomegaet, Pattaradra,Kulvaranon, Panisanun,Pandey, Aditi,Chobtumskul, Kittithorn,Tungsirisurp, Sireethorn,Sophanpanichkul, Punyanuch,Losuwanakul, Satreerat,Soimaneewan, Dechathon,Kanjanwongpaisan, Patcharida,Siricharoensang, Pornpawit,Choosakoonkriang, Sirirat
-
-
Read Online
- Synthesis of new 3-(2-Chloroquinolin-3-yl)-5-phenylisoxazole derivatives via click chemistry approach
-
Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3- yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline- 3-carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.
- Ferna?ndez-Galleguillos, Carlos,Saavedra, Luis A.,Gutierrez, Margarita
-
-
Read Online
- A new regioselective bromination of activated aromatic rings
-
An efficient and highly regioselective bromination of activated aromatic rings promoted by tribromoisocyanuric acid by in situ generation of Br + has been developed. A range of aromatic compounds were reacted with tribromoisocyanuric acid and trichloroisocyanuric acid and sodium bromide. Georg Thieme Verlag Stuttgart.
- De Almeida, Leonardo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
-
-
Read Online
- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
-
Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
-
-
Read Online
- Competitive Deprotonation and Superoxide [O2 -?] Radical-Anion Adduct Formation Reactions of Carboxamides under Negative-Ion Atmospheric-Pressure Helium-Plasma Ionization (HePI) Conditions
-
Carboxamides bearing an N-H functionality are known to undergo deprotonation under negative-ion-generating mass spectrometric conditions. Herein, we report that N-H bearing carboxamides with acidities lower than that of the hydroperoxyl radical (HO-O?) preferentially form superoxide radical-anion (O2 -?) adducts, rather than deprotonate, when they are exposed to the glow discharge of a helium-plasma ionization source. For example, the spectra of N-alkylacetamides show peaks for superoxide radical-anion (O2 -?) adducts. Conversely, more acidic amides, such as N-alkyltrifluoroacetamides, preferentially undergo deprotonation under similar experimental conditions. Upon collisional activation, the O2 -? adducts of N-alkylacetamides either lose the neutral amide or the hydroperoxyl radical (HO-O?) to generate the superoxide radical-anion (m/z 32) or the deprotonated amide [m/z (M - H)-], respectively. For somewhat acidic carboxamides, the association between the two entities is weak. Thus, upon mildest collisional activation, the adduct dissociates to eject the superoxide anion. Superoxide-adduct formation results are useful for structure determination purposes because carboxamides devoid of a N-H functionality undergo neither deprotonation nor adduct formation under HePI conditions. [Figure not available: see fulltext.]
- Hassan, Isra,Pinto, Spencer,Weisbecker, Carl,Attygalle, Athula B.
-
-
Read Online
- N-aryl-2-aminobenzimidazoles: Novel, efficacious, antimalarial lead compounds
-
From the phenotypic screening of the AstraZeneca corporate compound collection, N-aryl-2-aminobenzimidazoles have emerged as novel hits against the asexual blood stage of Plasmodium falciparum (Pf). Medicinal chemistry optimization of the potency against Pf and ADME properties resulted in the identification of 12 as a lead molecule. Compound 12 was efficacious in the P. berghei (Pb) model of malaria. This compound displayed an excellent pharmacokinetic profile with a long half-life (19 h) in rat blood. This profile led to an extended survival of animals for over 30 days following a dose of 50 mg/kg in the Pb malaria model. Compound 12 retains its potency against a panel of Pf isolates with known mechanisms of resistance. The fast killing observed in the in vitro parasite reduction ratio (PRR) assay coupled with the extended survival highlights the promise of this novel chemical class for the treatment of malaria.
- Ramachandran, Sreekanth,Hameed P., Shahul,Srivastava, Abhishek,Shanbhag, Gajanan,Morayya, Sapna,Rautela, Nikhil,Awasthy, Disha,Kavanagh, Stefan,Bharath, Sowmya,Reddy, Jitendar,Panduga, Vijender,Prabhakar,Saralaya, Ramanatha,Nanduri, Robert,Raichurkar, Anandkumar,Menasinakai, Sreenivasaiah,Achar, Vijayashree,Jiménez-Díaz, María Belén,Martínez, María Santos,Angulo-Barturen, I?igo,Ferrer, Santiago,Sanz, Laura María,Gamo, Francisco Javier,Duffy, Sandra,Avery, Vicky M.,Waterson, David,Lee, Marcus C. S.,Coburn-Flynn, Olivia,Fidock, David A.,Iyer, Pravin S.,Narayanan, Shridhar,Hosagrahara, Vinayak,Sambandamurthy, Vasan K.
-
-
Read Online
- Syntheses, Structural Characterization, Reactivity, and Theoretical Studies on Some Heteroligand Oxoperoxotungstate(VI)
-
White microcrystalline diamagnetic oxoperoxotungstate(VI) complexes K[WO(O2)2F]·H2O, K2[WO(O2)2(CO3)]·H2O, [WO(O2)(SO4)(H2O)2] have been synthesized from reaction of Na2WO4·2H2O with aqueous HF, solid KHCO3, aqueous H2SO4 (W:F? 1:3; W: CO3 2 ? 1:1; and W: SO4 2 ? 1:3), and an excess of 30% H2O2 at pH 7.5–8. Precipitation was completed by the addition of precooled acetone. The occurrence of terminal W?O and triangular bidentate O2 2 ?(C 2 v) in the synthesized compounds was ascertained from IR spectra. The IR spectra also suggested that the F? and SO4 2 ? ions in K[WO(O2)2F]·H2O and [WO(O2)(SO4)(H2O)2] were bonded to the WO +4 center in monodentate manner, while CO3 2 ? ion in K2[WO(O2)2(CO3)]·H2O binds the metal center in bidentate chelating fashion. The complex [WO(O2)(SO4)(H2O)2] is stable upto 110°C. The water molecule in [WO(O2)(SO4)(H2O)2] is coordinated to the WO +4 center, whereas it occurs as water of crystallization in the corresponding peroxo(fluoro) and peroxo(carbonato) compounds. Mass spectra of the compounds are in good agreement with the molecular formulae of the complexes. K2[WO(O2)2(CO3)]·H2O acts as an oxidant for bromide in the aqueous-phase bromination of organic substrates to the corresponding bromo-organics, and the complex also oxidizes Hantzsch-1,4-dihydropyridine to the corresponding pyridine derivative in excellent yield at room temperature. Density functional theory computation was carried out to compute the frequencies of relevant vibrational modes and electronic properties, and the results are in agreement with the experimentally obtained data.
- Das, Nandita,Chowdhury, Shubhamoy,Dutta Purkayastha, Ranendra N.
-
-
Read Online
- Fast and efficient bromination of aromatic compounds with ammonium bromide and Oxone
-
A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. Georg Thieme Verlag Stuttgart . New York.
- Naresh, Mameda,Arun Kumar, Macharla,Mahender Reddy, Marri,Swamy, Peraka,Nanubolu, Jagadeesh Babu,Narender, Nama
-
-
Read Online
- Hydrochloric acid catalysis of N-bromosuccinimide (NBS) mediated nuclear aromatic brominations in acetone
-
Nuclear bromination of activated aromatic substrates can be achieved quickly and in high yields using N-bromosuccinimide (NBS) in acetone with 1 M HCl catalysis.
- Andersh, Brad,Murphy, Drew L.,Olson, Ryan J.
-
-
Read Online
- H2O2/SOCl2: a useful reagent system for the conversion of thiocarbonyls to carbonyl compounds
-
The H2O2/SOCl2 reagent system has been used as a new and efficient reagent for deprotection of thiocarbonyls to carbonyl compounds. The salient features of this protocol are short reaction times, good chemoselectivity, clean reaction profiles, and simple work-up that preclude the use of toxic solvents.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Farrokhi, Azita
-
-
Read Online
- An instant and facile bromination of industrially-important aromatic compounds in water using recyclable CaBr2-Br2 system
-
Various industrially-important brominated intermediates have been instantly synthesized using aq. CaBr2-Br2 system as an efficient and recyclable brominating reagent under aqueous conditions at room temperature without the need for metal catalysts or acidic additives. Structurally-diverse phenol and aniline derivatives with strong electron-withdrawing groups such as carboxylic, nitro and formyl show remarkable reactivity to the brominating reagent and brominated in 92-98% yield with high purity (>99%) in a very short reaction time. Organic solvent-free conditions, a feature of the green chemistry, were successively used not only for the reactions but also for the isolation of products at the end of the reaction. The recycling of HBr by its neutralization, thereby generating additional amounts of industrially-important CaBr2 has been designed and developed. The brominating reagent has been recycled and regenerated, and the process was repeated up to 4 cycles after the fresh batch using the regenerated brominating reagent having almost identical selectivity and isolated yields, which seems to be the most promising methodology from the viewpoint of the green approach to organic synthesis.
- Kumar, Lalit,Mahajan, Tanu,Agarwal
-
-
Read Online
- Efficient nitriding reagent and application thereof
-
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
- -
-
Paragraph 0128-0130
(2021/03/31)
-
- Dehydrative Beckmann rearrangement and the following cascade reactions
-
The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.
- Liu, Yinghui,Wei, Yongjiao,Xie, Lan-Gui
-
supporting information
(2021/11/16)
-
- Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions
-
A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.
- Budnikova, Yulia,Kononov, Alexander,Rizvanov, Ildar,Strekalova, Sofia
-
p. 37540 - 37543
(2021/12/07)
-
- Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides
-
The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.
- Gudun, Kristina A.,Hayrapetyan, Davit,Khalimon, Andrey Y.,Segizbayev, Medet,Slamova, Ainur,Zakarina, Raikhan
-
-
- Evaluation of a Continuous-Flow Photo-Bromination Using N -Bromosuccinimide for Use in Chemical Manufacture
-
A continuous-flow photo-bromination reaction on benzyl and phenyl groups was conducted using N-bromosuccinimide as the bromine source inside a preparatory-scale glass plate reactor. This flow reactor system was capable of independently controlling light intensity, wavelength, and reaction temperature, hence exerting an exceptional level of control over the reaction. A short optimisation study for the synthesis of 2-bromomethyl-4-trifluoromethoxyphenylboronic acid pinacol ester resulted in best conditions of 20°C and 10 min residence time using an LED (light-emitting diode) array at 405 nm and acetonitrile as the solvent. The present study evaluates the potential for this easy-to-handle bromination system to be scaled up for chemical manufacture inside a continuous-flow glass plate reactor. The combination with an in-line continuous flow liquid-liquid extraction and separation system, using a membrane separator, demonstrates the potential for continuous flow reaction with purification in an integrated multi-stage operation with minimal manual handling in between.
- Waterford, Matthew,Saubern, Simon,Hornung, Christian H.
-
p. 569 - 573
(2021/04/16)
-
- Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds
-
We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.
- Ran, Maogang,He, Jiaxin,Yan, Boyu,Liu, Wenbo,Li, Yi,Fu, Yunfen,Li, Chao-Jun,Yao, Qiuli
-
supporting information
p. 1970 - 1975
(2021/03/16)
-
- A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
-
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
- Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 1955 - 1958
(2021/03/02)
-
- Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
-
A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
- Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
-
p. 2820 - 2826
(2021/02/01)
-
- An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition
-
We report acylation of alcohols and amines employing acetic acid as an acylating agent in solvent free condition by using alum doped nanopolyaniline (NDPANI) as a catalyst. This environmentally benign method does not use corrosive acid anhydrides and acid chlorides for acylation and does not produce waste product. Also, a non-toxic potash alum was used for doping of polyaniline rather than corrosive acids. The reaction conditions represent an advance over established method not only in omitting the need for expensive catalysts or solvents but also in shortening the reaction time significantly. The advantages of this catalyst are non-hazardous, cheap, reusable, easy to prepare and handling.
- Behera, Satyaranjan,Patra, Braja N.
-
-
- Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines
-
Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.
- Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush
-
-
- The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors
-
Three new dyes containing diphenylamine as electron donor, benzene (BIM1), benzothiadiazole (BTD) (BIM2) and N-ethylhexylbenzotriazole (BTZ) (BIM3) as auxiliary electron acceptors, quinoline as π-bridge and cyanoacrylic acid as anchoring group were synthesized in D-A-π-A structure for use in dye-sensitized solar cells (DSSCs). The optical, electrochemical, theoretical and photovoltaic methods were performed to understand the auxiliary acceptor influence on the performance of these dyes. Compared to the other dyes, the DSSC with dye BIM3 slightly increases the open circuit voltage (Voc) owing to the retardation of charge recombination by BTZ. However, replacement of benzene or BTZ by BTD unit causes a large red shift of the absorption spectra, leading BIM2 cell to produce the highest short circuit current density (Jsc). Thus, among the three D-A-π-A dyes, BIM2 is determined to be the most efficient dye, which reached a Voc of 0.627 V and Jsc of 11.53 mA cm–2, corresponding to an overall power conversion efficiency of 5.21 % in the presence of chenodeoxycholic acid (CDCA) as the coadsorbent. These results suggest that the insertion of benzothiadiazole as auxiliary acceptor into quinoline-based D-A-π-A dyes can effectively improve photovoltaic performance of DSSCs.
- ?i?man, ?lkay,Arkan, Burcu,Arslan, Bar?? Se?kin,Avc?, Davut,Derin, Yavuz,Gezgin, Merve,Nebio?lu, Mehmet,Tutar, Ahmet
-
-
- Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water
-
Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
-
p. 3289 - 3312
(2021/05/11)
-
- Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
-
A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
- Krishnappagowda, Lokanath Neratur,Kumar, Vasantha,Pai, Vinitha R.,Poojary, Boja,Rai, Vaishali M.,Shivalingegowda, Naveen,Udupi, Vishwanatha
-
-
- Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
-
The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
- Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.
-
supporting information
(2021/11/09)
-
- Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception
-
A method for Beckmann rearrangement using ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino) acetate (o-NosylOXY) under microwave irradiation is reported. Ketoximes (19 examples) are converted to the corresponding amides/lactams with 69–97% yields in ～10 minutes without any Lewis acid or co-catalyst. This is an example of halogen-free organocatalytic Beckmann rearrangement. Nuclear magnetic resonance (NMR)- and high-resolution mass spectrometry (HRMS)-based detailed mechanistic investigation suggest that o-NosylOXY acts as an initiator. Such initiators are reported before based on density functional theory (DFT) calculations. However, we report here the HRMS signatures of two transient intermediates, the nitrilium ion and the nitrilium ion's dimeric species. Rigorous NMR-based investigation of the reaction mechanism is performed. Our results indicate that the reported Beckmann rearrangement proceeds via two consecutive rearrangements. (Figure presented.).
- Dev, Dharm,Kalita, Tapasi,Mondal, Tanmay,Mandal, Bhubaneswar
-
p. 1427 - 1435
(2021/01/04)
-
- Visible light-induced mono-bromination of arenes with BrCCl3
-
A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.
- Fan, Jiali,Wei, Qiancheng,Zhu, Ershu,Gao, Jing,Cheng, Xiamin,Lu, Yongna,Loh, Teck-Peng
-
supporting information
p. 5977 - 5980
(2021/06/18)
-
- Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction
-
An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.
- Chaturvedi, Jagriti,Haldar, Chabush,Bisht, Ranjana,Pandey, Gajanan,Chattopadhyay, Buddhadeb
-
supporting information
p. 7604 - 7611
(2021/05/26)
-
- Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
-
Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.
- Chen, Yujie,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
-
p. 8226 - 8235
(2021/06/28)
-
- Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
-
Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.
- Pandia, Biplab Keshari,Gunanathan, Chidambaram
-
p. 9994 - 10005
(2021/07/31)
-
- Preparation method of acetamide compound
-
The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.
- -
-
Paragraph 0035-0047
(2021/05/19)
-
- An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism
-
Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.
- Tang, Li,Wang, Zhi-Lv,He, Yan-Hong,Guan, Zhi
-
p. 4929 - 4936
(2020/08/21)
-
- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
-
The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
-
supporting information
p. 281 - 285
(2020/01/28)
-
- A scalable and green one-minute synthesis of substituted phenols
-
A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.
- Elumalai, Vijayaragavan,Hansen, J?rn H.
-
p. 40582 - 40587
(2020/11/18)
-
- A one pot protocol to convert nitro-arenes into: N-aryl amides
-
A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
- Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
-
p. 4040 - 4044
(2020/02/04)
-
- Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis
-
Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.
- Morisset, Eléonore,Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me
-
supporting information
p. 388 - 392
(2020/01/24)
-
- N-acetylation of amines in continuous-flow with acetonitrile—no need for hazardous and toxic carboxylic acid derivatives
-
A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield.
- Fül?p, Ferenc,Mándity, István M.,Orsy, Gy?rgy
-
-
- An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives
-
A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.
- Vodnala, Nagaraju,Gujjarappa, Raghuram,Polina, Saibabu,Satheesh, Vanaparthi,Kaldhi, Dhananjaya,Kabi, Arup K.,Malakar, Chandi C.
-
supporting information
p. 20940 - 20944
(2020/12/31)
-
- Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: Redox properties in the fast synthesis of: N -arylacetamides and indolo(pyrrolo)[1,2- a] quinoxalines
-
In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and N-arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-a]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1H-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.
- Bejarano, Oscar Rodríguez,Ochoa-Puentes, Cristian,Pe?a-Solórzano, Diana,Trujillo, Sergio Alfonso
-
p. 40552 - 40561
(2020/11/18)
-
- Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones
-
Thiamine hydrochloride catalyzed synthesis of amides from ketones including 3-acetyl coumarin via Beckmann rearrangement has been reported. The reaction is believed to involve oxime formation, cleavage of C[sbnd]C bond followed by C[sbnd]N bond formation in one-pot. Thiamine hydrochloride is stable, cheap, easy to handle and environmentally friendly.
- Mahajan, Sheena,Slathia, Nancy,Kapoor, Kamal K.
-
supporting information
(2020/04/08)
-
- Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine
-
The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.
- Chandra, Dinesh,Verma, Saumya,Pandey, Chandra Bhan,Yadav, Ajay K.,Kumar, Puneet,Tiwari, Bhoopendra,Jat, Jawahar L.
-
supporting information
(2020/03/23)
-
- Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media
-
A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.
- Verma, Saumya,Kumar, Puneet,Khatana, Anil K.,Chandra, Dinesh,Yadav, Ajay K.,Tiwari, Bhoopendra,Jat, Jawahar L.
-
p. 3272 - 3276
(2020/11/02)
-
- Electrochemical formation of: N, N ′-diarylhydrazines by dehydrogenative N-N homocoupling reaction
-
Hydrazines represent a class of compounds of high interest due to their applicability as versatile starting materials in many important transformations. Herein, we report a synthetic approach to hydrazine derivatives using commercially available anilines and an anodic dehydrogenative N-N coupling reaction as the key step.
- Breising, Valentina M.,Kayser, Jacob M.,Kehl, Anton,Schollmeyer, Dieter,Liermann, Johannes C.,Waldvogel, Siegfried R.
-
supporting information
p. 4348 - 4351
(2020/04/27)
-
- Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
-
Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
- Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
-
supporting information
p. 12460 - 12469
(2020/06/10)
-
- Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles
-
Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.
- Xu, Jiaxi,Gao, Yu,Li, Zhenjiang,Liu, Jingjing,Guo, Tianfo,Zhang, Lei,Wang, Haixin,Zhang, Zhihao,Guo, Kai
-
p. 311 - 315
(2020/01/25)
-
- Visible-light-induced Beckmann rearrangement by organic photoredox catalysis
-
A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.
- Tang, Li,Wang, Zhi-Lv,Wan, Hai-Lan,He, Yan-Hong,Guan, Zhi
-
supporting information
p. 6182 - 6186
(2020/09/01)
-
- Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent
-
A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.
- Arrieta, Ana,Cossío, Fernando P.,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina
-
p. 2142 - 2150
(2020/03/11)
-
- HETEROCYCLIC COMPOUNDS AS MUTANT IDH INHIBITORS
-
The present disclosure relates generally to compounds useful in treatment of conditions associated with mutant isocitrate dehydrogenase (mt-IDH), particularly mutant IDH1 enzymes. Specifically, the present invention discloses compound of formula (IA), which exhibits inhibitory activity against mutant IDH1 enzymes. Method of treating conditions associated with excessive activity of mutant IDH1 enzymes with such compound is disclosed. Uses thereof, pharmaceutical composition, and kits are also disclosed.
- -
-
Paragraph 0423-0424
(2020/07/16)
-
- COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY
-
The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a PD-1 signaling inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and the PD-1 signaling inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a PD-1 signaling inhibitor and a pharmaceutically acceptable carrier or excipient.
- -
-
Paragraph 0128
(2020/04/09)
-
- N2-carbamylaryl-2-aminopyrimidine derivative and medical application thereof
-
The invention provides an N2-carbamylaryl-2-aminopyrimidine derivative and a medical application thereof. The N2-carbamylaryl-2-aminopyrimidine derivative provided by the invention comprises an optical isomer of the N2-carbamylaryl-2-aminopyrimidine derivative and pharmaceutically acceptable salt thereof. Pharmacodynamic research shows that the traditional Chinese medicine composition has no toxicor side effect, the compound has an FLT3 inhibitory activity. The proliferation inhibition activity is realized on various leukemia cell strains; a medium inhibition effect is achieved on breast cancer cells; moreover, the polypeptide is effective for multiple mutations of AML, such as internal tandem repeat mutation of a near-membrane structural domain and D835 point mutation of an activated ring in a kinase structural domain, almost has no inhibition effect on c-KIT, can overcome drug resistance brought by clinical point mutation, can reduce toxic and side effects of bone marrow inhibition,and can be applied to preparation of antitumor drugs. The structures of the general formulas Ia and Ib of the N2-carbamylaryl-2-aminopyrimidine derivative are shown in the specification,
- -
-
Paragraph 0037; 0040-0041; 0112-0113
(2020/10/28)
-
- GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
-
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
- -
-
Paragraph 001137; 001138; 001156; 001157
(2021/01/22)
-
- Citric acid stabilized on the surface of magnetic nanoparticles as an efficient and recyclable catalyst for transamidation of carboxamides, phthalimide, urea and thiourea with amines under neat conditions
-
Abstract: Citric acid-coated magnetic nanoparticles (Fe3O4–CA NPs) were successfully prepared and characterized. This magnetic nanocatalyst was employed as an efficient, recyclable, and environmentally benign heterogeneous catalyst for the transamidation of carboxamides, phthalimide, urea and thiourea with amines. Several derivatives of formylated and transamidated products were synthesized in good to excellent yields in the presence of this catalytic system. And, the catalyst could be easily separated from the reaction mixture using an external magnet and can be reused six times without any significant loss in its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
- Arefi, Marzban,Kazemi Miraki, Maryam,Mostafalu, Ramin,Satari, Mohammad,Heydari, Akbar
-
p. 393 - 400
(2019/01/28)
-
- o-Phthalic Anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement under mild conditions
-
o-Phthalic anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement was developed, producing the corresponding amide in up to 99% yield with acid-sensitive functionalities tolerated well, and the scale of the reaction could be enlarged to 77 mmol and the excellent yield was maintained. A successive procedure was developed. Moreover, the reaction was carried out at rt under nearly neutral conditions, and the workup was concise. These features illustrated the potential of the protocol in amide synthesis.
- Xu, Ze-Feng,Zhang, Teng,Hong, Wenjun
-
supporting information
p. 3113 - 3117
(2019/05/08)
-
- NOVEL PREPARATION METHOD FOR ACETAMINOPHEN
-
The present invention relates to a novel method for preparing acetaminophen, and more specifically, to a method for preparing acetaminophen, comprising the steps of: reacting a benzene compound substituted with a specific functional group and acetamide in the presence of a metal catalyst; and preparing acetaminophen by reacting a product and an aqueous solution in the presence of a metal catalyst and a base. Particularly, the present invention relates to a method for preparing acetaminophen which is environmentally friendly since a strong base is not used during a preparation process, and efficient and economical since acetaminophen can be prepared in a high yield while omitting separation of position isomers.
- -
-
Paragraph 0056-0060; 0067-0070
(2019/08/26)
-
- Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
-
Amide bond formation is one of the most important basic reactions in chemistry. A catalyst-free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro-oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.
- Tang, Li,Matuska, Jack H.,Huang, Yu-Han,He, Yan-Hong,Guan, Zhi
-
p. 2570 - 2575
(2019/06/13)
-
- Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study
-
A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.
- Zhao, Hong-Yi,Yang, Xue-Yan,Lei, Hao,Xin, Minhang,Zhang, San-Qi
-
p. 1406 - 1415
(2019/05/01)
-
- Copper-Catalyzed Site-Selective Oxidative C?C Bond Cleavage of Simple Ketones for the Synthesis of Anilides and Paracetamol
-
A copper-catalyzed approach for the N-acylation of anilines with acetone and acetophenones via C?C bond cleavage is described. Under the developed conditions both CHCl3 and CH2Cl2 were identified as potential C1-source to promote the transformation. The reaction features a site selective C?C bond cleavage to install the amide moieties with high functional-group compatibility and wide substrate scope. The developed method avoids the use of sensitive and narcotic agents. The method also represents an excellent complement to the previous protocols with lower E-factor (13.91 mg/1 mg) than current industrially used method (E-factor 17.54 mg/1 mg). The developed approach has also been extended for the effective preparation of pyridine derivatives and paracetamol in gram scale. The course of the reaction was monitored by 1H NMR as a preliminary investigation of the reaction mechanism. (Figure presented.).
- Vodnala, Nagaraju,Gujjarappa, Raghuram,Hazra, Chinmoy K.,Kaldhi, Dhananjaya,Kabi, Arup. K.,Beifuss, Uwe,Malakar, Chandi C.
-
supporting information
p. 135 - 145
(2018/12/05)
-
- An alternative way to analogues of avenanthramides and their antiradical activity
-
Abstract: The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied. Graphical abstract: [Figure not available: see fulltext.].
- Mierina, Inese,Stikute, Agnese,Mishnev, Anatoly,Jure, Mara
-
-
- Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions
-
An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.
- Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na
-
supporting information
p. 2169 - 2172
(2019/11/25)
-
