cas 29289-13-2, 2-IODO-4-METHYLANILINE | Articles data

Articles about 29289-13-2Total 70 be found

Article title
Article abstract
Author
Journal number and time
Download

Design of a fused triazolyl 2-quinolinone unnatural nucleoside via tandem CuAAC-Ullmann coupling reaction and study of photophysical property
This report presents the design and synthesis of a novel fused triazolyl 2-quinolinone (FTQuon) nucleoside as a new generation of angularly widened unnatural nucleobase surrogate with two possible H-bonding faces-one H-bond acceptor and another donor. The
Bag, Subhendu Sekhar,Das, Suman Kalyan,Gogoi, Hiranya
p. 2218 - 2229
(2018)
Read Online

Au(I)-Catalyzed 6-endo-dig Cyclizations of Aromatic 1,5-Enynes to 2-(Naphthalen-2-yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives
A gold(I)-catalyzed 6-endo-dig cyclization of aromatic 1,5-enynes was developed to synthesize 2-(naphthalen-2-yl)anilines. The functional group tolerance of this cyclization was examined systematically and a possible mechanism was proposed. The derivatization of 2-(naphthalen-2-yl)aniline was carried out to facile access to benzo[α]carbazole, benzo[c,h]cinnoline and dibenzo[i]phenanthridine derivatives in a divergent way.
Fu, Jiayue,Li, Bingbing,Wang, Xiugui,Liang, Qida,Peng, Xiaoshi,Yang, Lu,Wan, Tao,Wang, Xinxiu,Lin, Bin,Cheng, Maosheng,Liu, Yongxiang
supporting information
p. 46 - 52
(2021/11/20)

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics
Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.
Bhardwaj, Nivedita,Goel, Bharat,Indra, Arindam,Jain, Shreyans K.,Singh, Ajit Kumar,Tripathi, Nancy
p. 14177 - 14183
(2021/08/16)

Electrophilically activated nitroalkanes in synthesis of 3,4-dihydroquinozalines
Nitroalkanes activated with polyphosphoric acid serve as efficient electrophiles in reactions with various nucleophilic amines. Strategically placed second functionality allows for the design of annulation reactions enabling preparation of various heterocycles. This strategy was employed to develop an innovative synthetic approach towards 3,4-dihydroquinazolines from readily available 2-(aminomethyl)anilines.
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Grishin, Igor Yu.,Malyuga, Vladimir V.,Nobi, Mezvah A.,Rubin, Michael
(2021/08/03)

A new 1,2,3-triazole-decorated imino-phenol: selective sensing of Zn2+, Cu2+and picric acid under different experimental conditions
A new 1,2,3-triazole-decorated imino-phenol1has been synthesized, characterized and employed in metal ion sensing. Compound1is weakly fluorescent in CH3CN-H2O (3?:?1, v/v, pH = 6.8, and 10 mM HEPES buffer containing 1% DMSO) and show
Ghosh, Sumit,Baildya, Nabajyoti,Ghosh, Kumaresh
p. 10923 - 10929
(2021/06/25)

Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused γ-Lactones fromN-(o-Ethynylaryl)acrylamides and Formamide
An ultrafast (10 s) methodology to construct novel highly functionalized 2-quinolinones fromN-(o-ethynylaryl)acrylamides (1,7-enynes) is described for the first time. Microwave irradiation enabled the ultrafast synthesis of 2-quinolinone-fused γ-lactones from Fenton’s reagents in formamide. After six key consecutive reactions, including a diastereoselective step, 2-quinolinone-fused γ-lactones were obtained in good overall yield (up to 46%; 10 s).
Sacchelli, Bruce A. L.,Rocha, Bianca C.,Andrade, Leandro H.
supporting information
p. 5071 - 5075
(2021/07/20)

New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies
Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.
Puli, Venkat Swamy,Kilaru, Suresh,Bhongiri, Yadagiri,Marri, Sreenath Reddy,Tripathi, Anuj,Chetti, Prabhakar,Chatterjee, Anindita,Vukoti, Kiran Kumar,Pola, Someshwar
(2021/08/30)

Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles
A Cu(II)-promoted synthesis of an aza-fused N-heterocycle having a benz-imidazopyridine scaffold is developed via an addition-cyclization reaction followed by an Ullmann-type C-N coupling between o-iodoanilines and γ-ketodinitriles. This protocol features a broad substrate scope, giving products in 32-84% yields. The compounds show excellent photoluminescence properties having two absorption maxima in the region between 270-280 and 338-350 nm and emission maxima in the range of 502-533 nm. The HOMO-LUMO energy gap of 3.49-3.57 eV was determined using Gaussian 09 at the B3LYP/6-31G (d, p) basis set level. We also demonstrated a few postsynthetic modifications.
Rakshit, Amitava,Dhara, Hirendra Nath,Alam, Tipu,Dahiya, Anjali,Patel, Bhisma K.
supporting information
p. 17504 - 17510
(2021/11/18)

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
Hussain, Anwar,Sarkar, Akash Mamon,Sereda, Grigoriy,Zefirov, Nikolai
p. 1140 - 1146
(2020/04/01)

A novel DMSO-assisted regioselective iodination of aniline analogues
A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.
Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye
(2020/10/05)

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes
The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.
Ji, Jieying,Jiang, Quanbin,Liang, Yaoyu,Luo, Jie,Zhang, Xiaoyan,Zhao, Xiaodan
supporting information
p. 4959 - 4964
(2020/02/11)

From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination
Benzofurans can undergo ring-opening by a palladium-catalyzed process resulting in C?O bond breaking. Benzofuran-tethered 2-iodoanilines give synthetically interesting 2-(3-indolylmethyl)phenols in an overall reductive process. Mechanistic studies suggest that this unusual reaction proceeds by carbopalladation of benzofuran giving a 3-palladated 2,3-dihydrobenzofuran intermediate, which then fragments by an uncommon trans-elimination of the phenoxide group β to the metal. In this transformation, N,N-diisopropylethylamine (DIPEA) acts as a base and as a reducing agent: it regenerates palladium(0) from palladium(II), thus allowing catalytic turnover. (Figure presented.).
Perego, Luca A.,Wagschal, Simon,Grüber, Raymond,Fleurat-Lessard, Paul,El Ka?m, Laurent,Grimaud, Laurence
supporting information
p. 151 - 159
(2018/12/05)

Intramolecular Hydroamination of Selenoalkynes to 2-Selenylindoles in the Absence of Catalyst
In this work, a series of 2-chalcogenylindoles was synthesized by an efficient methodology, starting from chalcogenoalkynes, including a previously unreported tellurium indole derivative. For the first time, these 2-substituted chalcogenylindoles were obtained in the absence of metal catalyst or base, under thermal conditions only. In addition, the results described herein represent a methodology with inverse regioselectivity for the chalcogen functionalization of indoles.
Coelho, Felipe L.,Gil, Eduarda S.,Gon?alves, Paulo F. B.,Campo, Leandra F.,Schneider, Paulo H.
supporting information
p. 8157 - 8162
(2019/05/29)

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information
p. 6001 - 6009
(2019/04/17)

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides
Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.
Ageshina, Alexandra A.,Chesnokov, Gleb A.,Topchiy, Maxim A.,Alabugin, Igor V.,Nechaev, Mikhail S.,Asachenko, Andrey F.
supporting information
p. 4523 - 4534
(2019/05/17)

One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis
A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew
p. 4629 - 4639
(2019/05/17)

Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
supporting information
p. 4941 - 4948
(2019/11/03)

Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes
Visible light-promoted and gold-photoredox-catalyzed reactions of heteroatom (N, S, Se, O) tethered alkynes with arenediazonium salts selectively proceeded to build vicinal diaryl-substituted 2H-benzo[e][1,2]thiazine 1,1-dioxides (benzosultams), benzoselenophenes, benzothiophenes, 4H-chromen-4-ones (flavones), 3H-indoles, 1H-isochromen-1-ones (isocoumarins), and 4H-thiochromen-4-ones (thioflavones). Moreover, the utility of functionalized 3H-indoles as precursors for further elaboration has been demonstrated with the switchable and facile preparation of 1H-indoles, 2-oxindoles, and 3-oxindolines. (Figure presented.).
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Herrera, Fernando,Lázaro-Milla, Carlos,Luna, Amparo
supporting information
p. 2640 - 2652
(2017/08/16)

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
supporting information
p. 2246 - 2252
(2017/03/17)

Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
supporting information
p. 3402 - 3405
(2017/07/15)

Synthesis of carbazoles based on gold-copper tandem catalysis
An efficient synthetic method for carbazoles has been developed employing diazo anilinoalkynes as substrates. Sequential activation of the orthogonal functional groups embedded in diazo anilinoalkyne substrates by tandem gold-copper catalysis leads to the formation of highly substituted carbazoles. Substrate scope reveals a broad tolerability toward the substitution on aryl groups.
Choi, Subin,Srinivasulu, Vunnam,Ha, Sujin,Park, Cheol-Min
supporting information
p. 3481 - 3484
(2017/03/29)

METHODS AND COMPOSITIONS FOR THE REMOVAL OF ALDEHYDE ADDUCTS AND CROSSLINKS FROM BIOMOLECULES
Methods are provided for reducing the number of aldehyde adducts and/or crosslinks from fixed biomolecules. In some cases, subject methods include contacting a sample having aldehyde fixed biomolecules (e.g., a biological sample such as a formalin fixed p
-
Page/Page column 52

(2016/04/10)

Cyclization of 2-Alkynyldimethylaniline on Gold(I) Cationic and Neutral Complexes
The cyclization reaction of 2-(1-hexynyl)dimethylaniline (S) on gold(I) has been studied by NMR spectroscopy, in order to characterize the ion pair structure of the product, [LAuSc]BF4. The latter is a good model for the catalytic in
Biasiolo, Luca,Belpassi, Leonardo,Gaggioli, Carlo Alberto,MacChioni, Alceo,Tarantelli, Francesco,Ciancaleoni, Gianluca,Zuccaccia, Daniele
p. 595 - 604
(2016/03/04)

A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
supporting information
p. 2127 - 2133
(2016/02/18)

Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
Praveen, Chandrasekar,Perumal
p. 855 - 864
(2016/03/15)

One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
supporting information
p. 10987 - 10999
(2016/11/28)

Highly regioselective indoline synthesis under nickel/photoredox dual catalysis
Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indic
Tasker, Sarah Z.,Jamison, Timothy F.
supporting information
p. 9531 - 9534
(2015/08/18)

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
p. 157 - 162
(2015/01/30)

Aryl diazonium nanomagnetic sulfate and potassium iodide: An iodination process
A simple and efficient procedure for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid, and potassium iodide under solvent-free conditions at room temperature.
Kolvari, Eskandar,Amoozadeh, Ali,Koukabi, Nadiya,Otokesh, Somayeh,Isari, Mohsen
supporting information
p. 3648 - 3651
(2014/06/23)

A highly regioselective synthesis of N-acyl-2-acyl(aroyl)indolium Chloride through Palladium-Copper Catalysis Followed by Friedel-Crafts Reaction
2-Trimethylsilylethynyl acetanilides, obtained from the palladium-catalyzed reactions of 2-iodoacetanilides with trimethylsilylacetylene, underwent Friedel-Crafts acylation reactions yielding the N-acyl-2-acyl(aroyl)indolium chlorides in good yields. Georg Thieme Verlag Stuttgart New York.
Khan, Md. Wahab,Akther, Arifa,Alam, Md. Shariful
supporting information
p. 831 - 834
(2014/04/17)

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol
An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.
Kahandal, Sandeep S.,Kale, Sandip R.,Gawande, Manoj B.,Zboril, Radek,Varma, Rajender S.,Jayaram, Radha V.
p. 6267 - 6274
(2014/01/23)

Gold(I)-catalyzed iodination of arenes
A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.
Leboeuf, David,Ciesielski, Jennifer,Frontier, Alison J.
supporting information
p. 399 - 402
(2014/03/21)

A direct access to bioactive fused N-heterocyclic acetic acid derivatives
A Cu-catalyzed new sequence involving the Ullmann type intermolecular C-C followed by an intramolecular C-N coupling and then intramolecular aza-Michael type addition (and oxidation) in a single pot afforded various fused N-heterocyclic acetic acid derivatives as inhibitors of PDE4. This journal is the Partner Organisations 2014.
Adepu, Raju,Rajitha,Ahuja, Dipali,Sharma, Atul Kumar,Ramudu,Kapavarapu, Ravikumar,Parsa, Kishore V. L.,Pal, Manojit
supporting information
p. 2514 - 2518
(2014/04/17)

TUNABLE PHENYLACETYLENE HOSTS
A compound, or a salt thereof, having the formula wherein Y is n is 1 or 2; each R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy,
-
Paragraph 0270

(2014/02/16)

Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines
This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.
Hoque, Mohammad Mazharol,Halim, Mohammad A.,Rahman, Mohammad Mizanur,Hossain, Mohammad Ismail,Khan, Md. Wahab
p. 367 - 374
(2013/11/19)

KI-VO(acac)2-H2O2-acoh, A new iodinating system for selective iodination at C-5 position of activated pyrimidinediones: A combined experimental and density functional study
KI-VO(acac)2-H2O2 in aqueous ethanolic medium with acetic acid as additive has been found to iodinate pyrimidinediones and aromatic amines. The methodology is mild, efficient, and environmentally benign. Density functional theory-based reactivity parameters support the experimentally observed reactivity of pyrimidinedione derivatives.
Saikia, Lakhinath,Talukdar, Dhrubajyoti,Deka, Ramesh C.,Thakur, Ashim J.
p. 1031 - 1038
(2013/10/21)

BORON-CONTAINING SMALL MOLECULES
This invention provides novel compounds, methods of using the compounds, and pharmaceutical formulations comprising the compounds.
-
Paragraph 0361; 0362; 0388; 0389

(2013/06/04)

Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes
Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.
Nouzarian, Mahboobe,Hosseinzadeh, Rahman,Golchoubian, Hamid
supporting information
p. 2913 - 2925
(2013/09/02)

Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives
Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.
Ishida, Tomonobu,Kikuchi, Satoshi,Tsubo, Tatsuyuki,Yamada, Tohru
supporting information
p. 848 - 851
(2013/03/28)

Consecutive gold(I)-catalyzed cyclization reactions of o -(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas: A one-pot synthesis of pyrimido[1,6- a ]indol-1(2 H)-ones and related systems
Treatment of readily available o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas such as 1 with the Au(I)-catalyst 11 affords, via a twofold cyclization process, the isomeric pyrimido[1,6-a]indol-1(2H)-one 3 in good yield.
Sharp, Phillip P.,Banwell, Martin G.,Renner, Jens,Lohmann, Klaas,Willis, Anthony C.
supporting information
p. 2616 - 2619
(2013/07/11)

Spiro heterocycles as potential inhibitors of SIRT1: Pd/C-mediated synthesis of novel N-indolylmethyl spiroindoline-3,2′-quinazolines
Novel N-indolylmethyl substituted spiroindoline-3,2′-quinazolines were designed as potential inhibitiors of SIRT1. These compounds were synthesized in good yields by using Pd/C-Cu mediated coupling-cyclization strategy as a key step involving the reaction of 1-(prop-2-ynyl)-1′H- spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione with 2-iodoanilides. Some of the compounds synthesized have shown encouraging inhibition of Sir 2 protein (a yeast homologue of mammalian SIRT1) in vitro and three of them showed dose dependent inhibition of Sir 2. The docking results suggested that the benzene ring of 1,2,3,4-tetrahydroquinazolin ring system of these molecules occupied the deep hydrophobic pocket of the protein and one of the NH along with the sulfonyl group participated in strong H-bonding interaction with the amino acid residues.
Rambabu,Raja, Guttikonda,Yogi Sreenivas,Seerapu,Lalith Kumar,Deora, Girdhar Singh,Haldar, Devyani,Rao, M.V.Basaveswara,Pal, Manojit
supporting information
p. 1351 - 1357
(2013/03/14)

A Green protocol for the bromination and iodination of the aromatic compounds using H5IO6/NaBr and H5IO 6/NaI in the water
Bromination and iodination of the aromatic compounds have efficiently been carried out at room temperature and 70 °C, respectively, in short reaction times using orthoperiodic acid/sodium bromide (1:2) and orthoperiodic acid/sodium iodide (1:2) in water to prepare the corresponding halo compounds with excellent yields.
Yousefi-Seyf, Jaber,Tajeian, Kazem,Kolvari, Eskandar,Koukabi, Nadiya,Khazaei, Ardeshir,Zolfigol, Mohammad Ali
p. 2619 - 2622
(2012/10/29)

A cooperative catalytic system of platinum/iridium alloyed nanoclusters and a dimeric catechol derivative: An efficient synthesis of quinazolines through a sequential aerobic oxidative process
A cooperative catalytic system of heterogeneous polymer-supported bi-metallic platinum/iridium (Pt/Ir) alloyed nanoclusters and 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1, 1′-spiro-bisindane (TTSBI) enabled the facile preparation of quinazoline derivatives with low catalyst loadings and broad substrate scope under mild aerobic oxidative conditions. The ability to perform the reaction in gram-scale and under open-air conditions highlights the synthetic application of this cooperative catalytic system. Copyright
Yuan, Hao,Yoo, Woo-Jin,Miyamura, Hiroyuki,Kobayashi, Shu
supporting information
p. 2899 - 2904
(2013/01/15)

Potassium tert-butoxide promoted intramolecular arylation via a radical pathway
Potassium tert-butoxide mediated intramolecular cyclization of aryl ethers, amines, and amides was efficiently performed under microwave irradiation to provide the corresponding products in high regioisomeric ratios. The reaction proceeds via single-electron transfer to initiate the formation of an aryl radical, followed by a kinetically favored 5-exo-trig and subsequent ring expansion.
Roman, Daniela Sustac,Takahashi, Yoko,Charette, Andre B.
supporting information; experimental part
p. 3242 - 3245
(2011/08/02)

Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate
An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.
Ganguly, Nemai C.,Barik, Sujoy Kumar,Dutta, Sanjoy
experimental part
p. 1467 - 1472
(2010/09/16)

Cyclizations via frustrated Lewis pairs: Lewis acid induced intramolecular additions of amines to olefins and alkynes
(Figure Presented) Intramolecular additions of amines to olefinic and acetylenic residues in the presence of B(C6F5)3 affords a "frustrated Lewis Pair" strategy to five- and six-membered-ring heterocyclic ammonium borate d
Voss, Tanja,Chen, Chao,Kehr, Gerald,Nauha, Elisa,Erker, Gerhard,Stephan, Douglas W.
supporting information; experimental part
p. 3005 - 3008
(2010/07/04)

Peroxide/potassium iodide redox systems for in situ oxyiodination of organic compounds under liquid-phase and solvent-free conditions
Iodination of certain aromatic amines and phenols are triggered by the oxidation of KI by peroxy compounds such as tert-butyl hydroperoxide ( tBuOOH) under liquid-phase and solvent-free conditions by grinding the reactants in a mortar with a pestle. The reactions afforded corresponding iodo derivatives in good yield with high regioselectivity (Table 1).
Venkateshwarlu, Gattu,Premalatha, Akarapu,Chakradhar, Anuganti,Rajanna, Kamatala Chinna,Prakash, Pondichery Kuppuswamy Sai
experimental part
p. 345 - 349
(2010/05/15)

An improved iodination of 2-amino-5-nitrobenzonitrile
-
Zhang, Ye,Ren, Tianrui,Zhu, Weiwen,Xie, Yanhong
p. 90 - 93
(2007/10/03)

Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction
(Chemical Equation Presented) Intramolecular hydroamination of alkynyl amides was effected by a catalytic amount of Et2Zn (20 mol %) to form indole derivatives, and a tandem cyclization/nucleophilic addition procedure involving reaction of the indole zinc salt intermediate with acid chlorides or halides was developed to provide an efficient approach to C3-substituted indole derivatives when an excess of Et2Zn (120 mol %) was used.
Yin, Yan,Ma, Wenying,Chai, Zhuo,Zhao, Gang
p. 5731 - 5736
(2008/02/09)

Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones
(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.
Trost, Barry M.,McClory, Andrew
p. 2074 - 2077
(2008/02/14)