cas 610-15-1, 2-NITROBENZAMIDE | Articles data

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METHODS OF CONTROLLING CROP PESTS USING AROMATIC AMIDE INSECT REPELLENTS, METHODS OF MAKING AROMATIC AMIDE INSECT REPELLENTS, AND NOVEL AROMATIC AMIDE INSECT REPELLENTS
Methods of protecting fruit crops from flying insect pests and of repelling flying insects using aromatic amide compounds are disclosed. The methods apply the compounds to various surfaces, such as the fruit crops, the ground or structures adjacent to the fruit crops, or an object, article, human skin or animal. The compounds have the formula RxC6Hy—C(═O)—N(Cy), where RxC6Hy is a substituted phenyl group, each R group is independently C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, (halogen-substituted) C1-C4 alkylsulfonyl, phenylsulfonyl, tolylsulfonyl, amino, mono- or di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl; x is an integer of 1 to 5; x+y=5; Cy is a C2-C8 (substituted) alkadiyl, a C4-C6 (substituted) alkenediyl, or a (substituted) diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)— that, along with the amide N atom, forms a non-aromatic cyclic group; and R′ is C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, or (substituted) benzyl.
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(2022/03/18)

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes
Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.
Chen, Xuenian,Kang, Jia-Xin,Ma, Yan-Na,Miao, Yu-Qi
supporting information
p. 3595 - 3599
(2021/06/06)

Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides
Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.
Mohammadi, Robabeh,Gholipour, Behnam,Alamgholiloo, Hassan,Rostamnia, Sadegh,Mohtasham, Hamed,Zonouzi, Afsaneh,Ramakrishna, Seeram,Shokouhimehr, Mohammadreza
(2021/04/27)

Conversions of aryl carboxylic acids into aryl nitriles using multiple types of Cu-mediated decarboxylative cyanation under aerobic conditions
Here, we used malononitrile or AMBN as a cyanating agent to develop efficient and practical protocols for Cu-mediated decarboxylative cyanations, under aerobic conditions, of aryl carboxylic acids bearing nitro and methoxyl substituents at the ortho position as well as of heteroaromatic carboxylic acids. These protocols involved economical methods to synthesize value-added aryl nitriles from simple and inexpensive raw materials. Further diversification of the 2-nitrobenzonitrile product was performed to highlight the practicality of the protocols. This journal is
Cai, Hu,Cao, Xihan,Fu, Zhengjiang,Guo, Shengmei,Wang, Shuiliang
p. 8381 - 8385
(2020/11/05)

Method for preparing aryl primary amide by adopting metal-catalyzed one-pot method
The invention discloses a method for synthesizing aryl primary amide by adopting a metal-catalyzed one-pot method. The method comprises the steps of: taking aryl bromidess as raw materials, allowing the aryl bromidess to react with a cyanide source under the action of a palladium catalyst, substituting bromine on an aromatic ring with cyano to obtain cyano aromatic hydrocarbon, directly adding anaqueous solution of alkali into the reaction solution without aftertreatment, and carrying out hydrolysis reaction to obtain aryl primary amide. Compared with the prior art, the method for preparing aryl primary amide from the aryl bromides has the advantages of the short synthesis route, fewer reaction steps, simple operation, mild conditions, the high conversion rate, low toxicity and industrialproduction potential.
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Paragraph 0041; 0042

(2020/04/06)

Glucose as an Eco-Friendly Reductant in a One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco-friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one-pot sequences involving glucose as a reductant.
dos Santos, Thiago,Grundke, Caroline,Lucas, Tobias,Gro?mann, Luca,Clososki, Giuliano Cesar,Opatz, Till
supporting information
p. 6429 - 6432
(2020/09/02)

Transamidation for the Synthesis of Primary Amides at Room Temperature
Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.
Chen, Jiajia,Lee, Sunwoo,Xia, Yuanzhi
supporting information

(2020/05/05)

A carboxylic acid continuous method of preparing amide (by machine translation)
The invention discloses a continuous process for preparing amides of carboxylic acid method, it comprises the following steps: raw material carboxylic acid with the catalyst is dissolved in a solvent as a material A, acyl acyl reagent or reagent is dissolved in a solvent as a material B, amine reagent or an amine reagent is dissolved in the water as the material C, material A and material B respectively through the infusion pump delivering it into a tubular reactor I acyl reaction, the obtained intermediate product acyl chloride by the infusion pump 3 conveying the material into the tubular reactor C together with the amination reaction II, the reaction mixture after flowing out of the tubular reactor II, through after treatment to obtain the target amide. The invention adopts the technical, can ensure that the whole process is continuous, controllable, raw materials less dose, high safety, and can be easily realized and hermetical, continuous, automated production; the invention through the use of low-cost proton acid catalytic reaction, its low cost, after treatment is simple, easy to separate and remove, from the source to avoid the generation of the carcinogen, consistent with the requirement of environmental protection. (by machine translation)
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(2019/05/16)

Ionic liquid catalysed aerobic oxidative amidation and thioamidation of benzylic amines under neat conditions
Tetrabutylammonium hydroxide (TBAOH) was discovered as a highly efficient and green catalyst for aerobic oxidation of the α-methylene carbon of primary amines as well as benzylic groups into the corresponding amides and ketones under neat conditions. We described herein, ionic liquid TBAOH catalysed aerobic oxidation of benzyl amines to benzamides and with elemental sulfur; the corresponding benzylbenzothioamides were obtained under metal-free, oxidant-free and base-free conditions. Applicability at the gram scale for the synthesis of the desired amides/ketones is also demonstrated with the present protocol.
Joshi, Abhisek,Kumar, Rahul,Semwal, Rashmi,Rawat, Deepa,Adimurthy, Subbarayappa
supporting information
p. 962 - 967
(2019/03/11)

(Ar-tpy)RuII(ACN)3: A Water-Soluble Catalyst for Aldehyde Amidation, Olefin Oxo-Scissoring, and Alkyne Oxygenation
The synthetic chemists always look for developing new catalysts, sustainable catalysis, and their applications in various organic transformations. Herein, we report a new class of water-soluble complexes, (Ar-tpy)RuII(ACN)3, utilizing designed terpyridines possessing electron-donating and -withdrawing aromatic residues for tuning the catalytic activity of the Ru(II) complex. These complexes displayed excellent catalytic activity for several oxidative organic transformations including late-stage C-H functionalization of aldehydes with NH2OR to valuable primary amides in nonconventional aqueous media with excellent yield. Its diverse catalytic power was established for direct oxo-scissoring of a wide range of alkenes to furnish aldehydes and/or ketones in high yield using a low catalyst loading in the water. Its smart catalytic activity under mild conditions was validated for dioxygenation of alkynes to highly demanding labile synthons, 1,2-diketones, and/or acids. This general and sustainable catalysis was successfully employed on sugar-based substrates to obtain the chiral amides, aldehydes, and labile 1,2-diketones. The catalyst is recovered and reused with a moderate turnover. The proposed mechanistic pathway is supported by isolation of the intermediates and their characterization. This multifaceted sustainable catalysis is a unique tool, especially for late-stage functionalization, to furnish the targeted compounds through frequently used amidation and oxygenation processes in the academia and industry.
Joarder, Dripta De,Gayen, Subrata,Sarkar, Rajarshi,Bhattacharya, Rajarshi,Roy, Sima,Maiti, Dilip K.
p. 8468 - 8480
(2019/07/03)

Method for preparing derivatives of benzamide under microwave condition in aqueous phase
The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.
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Paragraph 0018; 0099

(2019/03/28)

Direct and facile synthesis of primary amides from carboxylic acids via acyl isocyanate intermediates using mukaiyama reagent
A very simple and efficient procedure for the preparation of primary amides is described from carboxylic acids using Mukaiyama reagent/KNCO in aqueous acetonitrile. Availability of the reagents, simplicity, and easy workup of the reaction crude make this method attractive for organic chemists.
Azadi, Roya,Motamedpoor, Zahra
p. 801 - 804
(2018/09/26)

Mechanochemical synthesis of primary amides from carboxylic acids using TCT/NH4SCN
A facile and effective approach toward the synthesis of primary amides from carboxylic acids has been developed. In the presence of 2,4,6-trichloro-1,3,5-triazine, a combination of ammonium thiocyanate and potassium carbonate led to the rapid conversion of carboxylic acids into the corresponding amides within five minutes grinding at room temperature. The use of ammonium thiocyanate as the amine source is unprecedented and exclusive formation of primary amides is observed only under the liquid-assisted grinding conditions.
Jaita, Subin,Phakhodee, Wong,Chairungsi, Neeranuch,Pattarawarapan, Mookda
supporting information
p. 3571 - 3573
(2018/09/10)

Transfer hydrogenation and hydration of aromatic aldehydes and nitriles using heterogeneous NiO nanofibers as a catalyst
A simple and efficient hydrogen transfer reaction of aldehydes and hydration of nitriles using nickel oxide nanofibers (NiO NFs) as a heterogeneous catalyst is reported. NiO NFs prepared by electrospinning technique was cubic (confirmed by XRD) with an average diameter of 80 nm (obtained from HR-TEM) and utilized as a nanocatalyst for heterogeneous transfer hydrogenation of aromatic aldehydes and hydration of aromatic nitriles. All the reaction products produced with minimum reaction time and maximum yield were confirmed using GC-MS with NIST library. Furthermore, heterogeneity of the catalyst was confirmed with ICP-MS analysis. The as-prepared catalyst was reused for six cycles and was found to be efficient. Hence, the present catalytic synthesis of alcohols and amides may be an economically viable process.
Thenmozhi,Kadirvelu
p. 15572 - 15577
(2018/10/04)

A continuous-flow synthesis of primary amides from hydrolysis of nitriles using hydrogen peroxide as oxidant
A continuous-flow synthesis of primary amides from hydrolysis of nitriles using hydrogen peroxide as oxidant has been developed. Using this procedure, a variety of nitriles could be smoothly transformed into the desired primary amides in good to excellent yields. The mild reaction conditions and the flowing reaction system greatly improved the safety and make the reaction easy to scale up.
Zhan, Wei,Ji, Ling,Ge, Ze-mei,Wang, Xin,Li, Run-tao
p. 1527 - 1532
(2018/02/21)

Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides
A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/H2O, 25 °C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.
Zhang, Zhiguo,Zheng, Dan,Wan, Yameng,Zhang, Guisheng,Bi, Jingjing,Liu, Qingfeng,Liu, Tongxin,Shi, Lei
p. 1369 - 1376
(2018/02/09)

Uniformly dispersed copper nanoparticles onto the modified magnetically recoverable nanocatalyst for aqueous synthesis of primary amides
Magnetically recoverable and environmentally friendly Cu-based heterogeneous catalyst has been synthesized for the one-pot conversion of aldehydes to their corresponding primary amides. The Fe3O4@SiO2 nanocomposites were prepared by synthesis of Fe3O4 magnetic nanoparticles (MNPs) which was then coated with a silica shell via St?ber method. Bi-functional cysteine amino acid was covalently bonded onto the siliceous shell of nanocatalyst. The CuII ions were then loaded onto the modified surface of nanocatalyst. Finally, uniformly dispersed copper nanoparticles were achieved by reduction of CuII ions with NaBH4. Amidation reaction of aryl halides with electron-withdrawing or electron-donating groups and hydroxylamine hydrochloride catalyzed with Fe3O4@SiO2@Cysteine-copper (FSC-Cu) MNPs in aqueous condition gave an excellent yield of products. The FSC-Cu MNPs could be easily isolated from the reaction mixture with an external magnet and reused at least 8 times without significant loss in activity.
Ziaee, Fariborz,Gholizadeh, Mostafa,Seyedi, Seyed Mohammad
(2017/09/06)

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Sharif, Muhammad,Kalevaru, Narayana V.,Jagadeesh, Rajenahally V.
supporting information
p. 266 - 273
(2018/01/12)

A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water
In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.
Sanz Sharley, Daniel D.,Williams, Jonathan M.J.
supporting information
p. 4090 - 4093
(2017/09/27)

Heteropolytungstostannate as a homo- and heterogeneous catalyst for Knoevenagel condensations, selective oxidation of sulfides and oxidative amination of aldehydes
Heteropolytungstostannate K11H[P2W18O68(HOSnIVOH)3]·20H2O (1) is used as a homo- and heterogeneous catalyst for Knoevenagel condensations. New Fe3O4@SiO2@CH2(CH2)2NH3+[P2W18O68(HOSnIVOH)3]11- nanocatalyst was fabricated through electrostatic grafting of (1) on amine-modified silica-coated magnetic nanoparticles. The new magnetically recoverable nanocatalyst was characterized using infrared spectroscopy (IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray powder diffractometry (XRD), energy-dispersive X-ray analysis (EDX) and alternating gradient force magnetometry (AGFM). The results indicate that the particles are mostly spherical in shape and have an average size of approximately 30 nm. The catalytic activity of the catalyst was investigated in the selective oxidation of sulfides to sulfoxides and oxidative amination of aldehydes in an aqueous medium. The catalyst was reused at least five times without significant decrease in catalytic activities, and the structure of the catalyst remained unchanged after recycling.
Khoshnavazi, Roushan,Bahrami, Leila,Rezaei, Manuchehr
p. 45495 - 45503
(2017/10/06)

Hexagonal Mesoporous Silica-Supported Copper Oxide (CuO/HMS) Catalyst: Synthesis of Primary Amides from Aldehydes in Aqueous Medium
Hexagonal mesoporous silica (HMS)-supported copper oxides (CuO/HMS) have been prepared by a sol–gel method and characterized by X-ray diffraction, FTIR spectroscopy, transmission electron microscopy, N2 sorption, inductively coupled plasma (ICP), X-ray photoelectron spectroscopy (XPS), H2 temperature-programed reduction (TPR), NH3 temperature-programed desorption (TPD), and high-resolution (HR)-TEM techniques. An analysis of these results revealed a mesoporous material system with a high surface area (974 m2 g?1) and uniform pore-size distribution. The catalytic efficacy of CuO on the HMS support with varying Cu loadings (1, 3, 5, 10, and 15 wt %) was investigated for the transformation of aldehydes to primary amides; 3 wt % CuO/HMS exhibited good catalytic performance with good to excellent yields of amides (60–92 %) in benign aqueous medium. The intrinsically heterogeneous catalyst could be recovered after the reaction and reused without any noticeable loss in activity.
Kadam, Ravishankar G.,Rathi, Anuj K.,Cepe, Klara,Zboril, Radek,Varma, Rajender S.,Gawande, Manoj B.,Jayaram, Radha V.
p. 467 - 473
(2017/04/13)

Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives
A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.
Song, Gaopeng,Li, Jianzuo,Tian, Hao,Li, Yasheng,Hu, Dekun,Li, Ying,Cui, Zining
p. 329 - 334
(2016/04/04)

Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety
A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.
He, Haifeng,Wang, Xiaoyan,Shi, Liqiao,Yin, Wenyan,Yang, Ziwen,He, Hongwu,Liang, Ying
p. 3263 - 3270
(2016/07/12)

Synthesis of and catalytic nitrile hydration by a cationic tris(μ-hydroxo)diruthenium(II) complex having PMe3ligands
While phenyl vinyl ether does not react with [Ru(η4-1,5-COD)(η6-1,3,5-COT)] (1)/PMe3, the C–O bond cleavage of phenyl vinyl ether occurs by 1/PMe3in the presence of water to give a tris(μ-hydroxo)diruthenium(II) complex [(Me3P)3Ru(μ-OH)3Ru(PMe3)3]+[OPh]?·HOPh (3·HOPh) with evolution of ethylene. The molecular structure of 3·HOPh is unequivocally determined by X-ray analysis. The most likely mechanism for the formation of 3·HOPh is protonation of [Ru(η4-1,5-COD)(PMe3)3] (2c) by water and subsequent insertion of phenyl vinyl ether into the resulting Ru–H bond followed by the β-phenoxide elimination and hydrolysis and dimerization of the phenoxoruthenium(II) species. Complex 3 acts as a catalyst for nitrile hydration. As a typical example, the hydration of benzonitrile was achieved by 3 (1.0 mol%) in 1,4-dioxane at 120 °C for 6 h to give benzamide quantitatively.
Kiyota, Sayori,Kobori, Takako,Soeta, Hirofumi,Ichikawa, You-ichi,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi
p. 3 - 10
(2016/12/06)

A method of from [...] amide
The invention discloses a method for synthesizing amides from oxime. The method is characterized by adding oxime, water and a water-soluble iridium complex catalyst to a reaction vessel, cooling a reactant to the room temperature after the reaction mixture reacts at 80-120 DEG C for several hours, removing water through selective evaporation, and obtaining a target product through column separation. Compared with existing methods for synthesizing amides through oxime rearrangement in water through transition metal catalysis, the method has the advantages that the used catalyst is low in load and does not contain phosphine ligands severely polluting the environment, so that the reaction can be carried out in the air, without nitrogen protection; therefore the reaction meets the green chemical requirements and has an extensive development prospect.
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Paragraph 0080-0084

(2017/01/31)

Direct oxidative esterification of alcohols and hydration of nitriles catalyzed by a reusable silver nanoparticle grafted onto mesoporous polymelamine formaldehyde (AgNPs@mPMF)
A nitrogen-rich mesoporous organic polymer was synthesized as a novel support. A silver nanoparticle was synthesized and grafted onto it. The prepared catalyst (AgNPs@mPMF) was characterized by powder X-ray diffraction (XRD), scanning electron microscopy(SEM) and energy dispersive X-ray spectrometry (EDS), thermogravimetric analysis (TGA), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflectance spectroscopy (DRS), N2 adsorption, Raman spectroscopy and EPR study. The catalytic activity was evaluated for the oxidative esterification reaction of alcohols and hydration of nitriles. The oxidative esterification reaction was carried out for various activated alcohols giving excellent yields of the corresponding ester products. The catalyst was also efficient in the hydration of nitriles. Both reactions were optimized by varying the bases, temperatures and solvents. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity and selectivity.
Ghosh, Kajari,Iqubal, Md. Asif,Molla, Rostam Ali,Mishra, Ashutosh,Kamaluddin,Islam, Sk Manirul
p. 1606 - 1622
(2015/04/27)

Selective NaOH-catalysed hydration of aromatic nitriles to amides
The selective synthesis of aromatic and heteroaromatic amides through base-catalysed hydration of nitriles was achieved using inexpensive and commercially available NaOH as the only catalyst. A wide range of nitriles was selectively converted to their corresponding amides. Kinetic studies show that the double hydration of nitriles towards undesirable carboxylic acids is negligible under our reaction conditions.
Schmid, Thibault E.,Gómez-Herrera, Alberto,Songis, Olivier,Sneddon, Deborah,Révolte, Antoine,Nahra, Fady,Cazin, Catherine S. J.
p. 2865 - 2868
(2015/05/27)

Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp3 C-H Functionalization
An efficient, metal-free domino protocol for the synthesis of benzamides has been developed from ethylarenes using aqueous ammonia. The reaction proceeds through the formation of triiodomethyl ketone intermediate in the presence of iodine as the promoter and TBHP as an oxidant followed by nucleophilic substitution with aqueous ammonia, forming an amide. This operationally simple, functional-group-tolerant tandem approach provides an easy access to the broad range of biologically important benzamides.
Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Prakash, Sattey,Chaskar, Atul C.
supporting information
p. 1677 - 1682
(2015/07/20)

Palladium(II) complexes with a phosphino-oxime ligand: Synthesis, structure and applications to the catalytic rearrangement and dehydration of aldoximes
The treatment of [PdCl2(COD)] (COD = 1,5-cyclooctadiene) with 1 and 2 equivalents of 2-(diphenylphosphino)benzaldehyde oxime in dichloromethane at room temperature led to the selective formation of [PdCl2{κ2-(P,N)-2-Ph2PC6H4CHNOH}] (1) and [Pd{κ2-(P,N)-2-Ph2PC6H4CHNOH}2][Cl]2 (2), respectively, which represent the first examples of Pd(II) complexes containing a phosphino-oxime ligand. These compounds, whose structures were fully confirmed by X-ray diffraction methods, were active in the catalytic rearrangement of aldoximes. In particular, using 5 mol% complex 1, a large variety of aldoximes could be cleanly converted into the corresponding primary amides at 100 °C, employing water as solvent and without the assistance of any cocatalyst. Palladium nanoparticles are the active species in the rearrangement process. In addition, when the same reactions were performed employing acetonitrile as solvent, selective dehydration of the aldoximes to form the respective nitriles was observed. For comparative purposes, the catalytic behaviour of an oxime-derived palladacyclic complex has also been briefly evaluated.
Menéndez-Rodríguez, Lucía,Tomás-Mendivil, Eder,Francos, Javier,Nájera, Carmen,Crochet, Pascale,Cadierno, Victorio
p. 3754 - 3761
(2015/07/01)

Efficient and selective copper-grafted nanoporous silica in aqueous conversion of aldehydes to amides
The one-pot conversion of aldehydes to their corresponding primary amides has been studied using SBA-15-grafted ethylenediamine copper complexes (En-Cu). The heterogeneous catalyst could be readily isolated from the reaction mixture and reused at least 14 times without significant loss in activity. The influence of reaction parameters was studied and the conditions determining yields and selectivities, including quantity of catalyst, solvent and base, were optimized to afford amides in high yields. The structures of synthesized catalysts were investigated using different characterization techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), CHN, atomic absorption (AA), scanning electron microscopy (SEM) and transmission electron microscopy (TEM).
Rostamnia, Sadegh,Nouruzi, Nasrin,Xin, Hongchuan,Luque, Rafael
p. 199 - 205
(2015/02/02)

Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines
A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.
Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
p. 900 - 907
(2015/02/19)

A phosphine-free approach to primary amides by palladium-catalyzed aminocarbonylation of aryl and heteroaryl iodides using methoxylamine hydrochloride as an ammonia equivalent
The palladium-catalyzed synthesis of primary amides by aminocarbonylation of aryl and heteroaryl iodides under phosphine-free conditions is reported for the first time. Methoxylamine hydrochloride, acting as an ammonia equivalent, undergoes sequential carbonylation and demethoxylation under mild reaction conditions. The procedure does not require a phosphine ligand and takes place in short reaction times at low temperatures to provide the products in excellent yields. Georg Thieme Verlag Stuttgart · New York.
Gadge, Sandip T.,Bhanage, Bhalchandra M.
p. 85 - 88
(2014/01/06)

Synthesis of primary Amides via Copper-Catalyzed Aerobic Decarboxylative ammoxidation of Phenylacetic Acids and α-Hydroxyphenylacetic acids with Ammonia in water
A Cu2O-catalyzed aerobic oxidative decarboxylative ammoxidation to primary benzamides from phenylacetic acids and a-hydroxyphenylacetic acids is developed. A variety of primary benzamides could be prepared smoothly, in good to excellent yields, by means of a one-pot domino protocol combining decarboxylation, dioxygen activation, oxidative C-H bond functionalization, and amidation reactions.
Song, Qiuling,Feng, Qiang,Yang, Kai
supporting information
p. 624 - 627
(2014/04/03)

Rearrangement of aldoximes to amides in water under air atmosphere catalyzed by water-soluble iridium complex [Cp*Ir(H2O) 3][OTf]2
In the presence of the water-soluble iridium complex [Cp*Ir(H 2O)3][OTf]2, a variety of aldoximes, including aromatic, aliphatic, conjugated unsaturated and non-conjugated unsaturated, were converted into their corresponding amides in water with good to excellent yields. Further, the one-pot synthesis of amides from aldehydes, hydroxylamine hydrochloride and sodium carbonate via a tandem condensation-rearrangement reaction in water was also accomplished. Compared with the reported organometallic catalysts for the rearrangement of aldoximes to amides in water, the present catalyst exhibited some advantages such as being phosphorus ligand-free, having low catalyst loading, and operational convenience under air atmosphere. This journal is the Partner Organisations 2014.
Sun, Chunlou,Qu, Panpan,Li, Feng
p. 988 - 996
(2014/04/03)

Chitosan supported ionic liquid: A recyclable wet and dry catalyst for the direct conversion of aldehydes into nitriles and amides under mild conditions
A green and highly efficient chitosan supported magnetic ionic liquid (CSMIL) was synthesized with chitosan (the most abundant biopolymer in nature and a cheap industrial waste product), methyl imidazole and anhydrous/hydrous FeCl3. The heterogeneous catalyst thus obtained was used for the direct conversion of aldehydes to the corresponding nitriles in the presence of NH2OH·HCl/dry-CSMIL/MeSO2Cl and amides with NH 2OH·HCl/wet-CSMIL/MeSO2Cl. A highlight of our approach is the easy separation of the catalyst from the reaction medium and thus the recyclability of the catalyst. This simple method can be applied to obtain a wide range of aromatic, heterocyclic, and aliphatic nitriles and amides.
Khalafi-Nezhad, Ali,Mohammadi, Somayeh
p. 13782 - 13787
(2014/04/17)

Copper-catalyzed aerobic oxidative synthesis of aryl nitriles from benzylic alcohols and aqueous ammonia
Copper-catalyzed direct conversion of benzylic alcohols to aryl nitriles was realized using NH3(aq.) as the nitrogen source, O2 as the oxidant and TEMPO as the co-catalyst. Furthermore, copper-catalyzed one-pot synthesis of primary aryl amides from alcohols was also achieved.
Tao, Chuanzhou,Liu, Feng,Zhu, Youmin,Liu, Weiwei,Cao, Zhiling
p. 3349 - 3354
(2013/06/05)

An efficient and practical protocol for catalytic hydrolysis of nitriles by a copper(I) complex in water
The cuprous complex - Cu4I4(H2O) 4 - has been isolated and employed for the catalytic hydrolysis of arenecarbonitriles, cinnamonitrile, and arylacetonitriles to the corresponding amides in pure water in high yields of up to 98%. The catalyst can be easily recovered and reused without loss of catalytic activity at least five times. Oxindole could be prepared successfully by one-pot domino protocols based on this method. Copyright
Li, Zhengkai,Wang, Lixia,Zhou, Xiangge
supporting information; experimental part
p. 584 - 588
(2012/05/19)

I2-TEMPO as an efficient oxidizing agent for the one-pot conversion of alcohol to amide using FeCl3 as the catalyst
A high yield one-pot method for the synthesis of amides from alcohols is described. The aldehyde was generated in situ using iodine-TEMPO as oxidizing agent followed by intermediate oxime formation through reaction with NH 2OH?HCl and finally rearrangement of oxime catalyzed by FeCl3.
Das, Rima,Chakraborty, Debashis
experimental part
p. 48 - 53
(2012/08/28)

Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
p. 6482 - 6490
(2012/10/30)

An efficient copper(II)-catalyzed direct access to primary amides from aldehydes under neat conditions
A simple expeditious one-pot conversion of a wide assortment of aldehydes to corresponding primary amides in good to excellent yields has been accomplished employing hydroxylamine hydrochloride (1 mol equiv), sodium acetate (1.1 mol equiv), and copper sulfate pentahydrate (5 mol %) under neat conditions at 110 °C. The protocol based upon ligand-free copper (II)-catalysis avoids the use of relatively expensive late transition metal-based catalysts, and is performed under operationally simple conditions without any demanding procedure of isolation and purification of products.
Ganguly, Nemai C.,Roy, Sushmita,Mondal, Pallab
experimental part
p. 1413 - 1416
(2012/03/27)

The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells
We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal antibody, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways.
Hour, Mann-Jen,Yang, Jai-Sing,Chen, Tai-Lin,Chen, Kuan-Tin,Kuo, Sheng-Chu,Chung, Jing-Gung,Lu, Chi-Cheng,Chen, Chia-Yi,Chuang, Yi-Hsuan
p. 2709 - 2721
(2011/06/27)

Efficient synthesis of primary amides from carboxylic acids using n,n'-carbonyldiimidazole and ammonium acetate in ionic liquid
A novel and efficient method for the conversion of carboxylic acids to primary amides using N,N'-carbonyldiimidazole in combination with ammonium acetate/triethyl amine system in [BMIM]BF4 is developed.
Lee, Kwan Soo,Kim, Kee D.
p. 3497 - 3500
(2011/09/30)

Highly efficient one-pot synthesis of primary amides catalyzed by scandium(III) triflate under controlled MW
The present Letter highlights a versatile synthetic protocol for the one-pot synthesis of primary amides employing scandium(III) triflate as a catalyst in water under controlled MW. This methodology offers excellent yields in shorter reaction times with enhanced selectivity.
Allam, Bharat Kumar,Singh, Krishna Nand
experimental part
p. 5851 - 5854
(2011/12/03)

FeIII-catalyzed synthesis of primary amides from aldehydes
A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. Copyright
Gowda, Ravikumar R.,Chakraborty, Debashis
supporting information; experimental part
p. 2226 - 2229
(2011/06/17)

Furan ring opening-pyrrole ring closure: A new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines
A method of synthesis of pyrrolo[1,2-a][1,4]benzodiazepines is described. This method is based on the recyclization of N-(furfuryl)anthranilamides under treatment with an aq. HCl/AcOH system and allows one to form both diazepine and pyrrole rings in one step. The reaction proceeds via furan ring opening into a diketone moiety followed by consecutive interaction of the NH2-group with both carbonyl functions. The process is not efficient in the presence of alkyl or aryl groups on amide nitrogen due to competitive furfuryl cation elimination. But alkylation of pyrrolo[1,2-a][1,4]benzodiazepines yields efficiently the corresponding N-alkyl derivatives. Steric effects also prevent cyclization due to reversibility of diazepine ring formation under these reaction conditions. However, the corresponding pyrrolo[1,2-a][1,4] benzodiazepines can be obtained by a stepwise process, i.e., 1) furan ring opening with aq. HCl/AcOH and 2) cyclization of isolated aminodiketones under treatment with glacial acetic acid. Another efficient procedure for the synthesis of pyrrolo[1,2-a][1,4]benzodiazepines consists of acid-catalyzed furan ring opening of N-(furfuryl)-2-nitrobenzamides followed by treatment of the formed nitrodiketone with Fe/AcOH. It leads to a one pot reduction of nitro group to amine, cyclization into diazepine and pyrrole ring formation. This procedure is efficient both for substrates with steric demands and for N-alkyl- or N-aryl-N-(furfuryl)amides. The proposed approach can be also applied to the synthesis of parent pyrrolo[1,2-a][1,4]diazepines or their analogues annulated to heterocycles. The Royal Society of Chemistry 2010.
Butin, Alexander V.,Nevolina, Tatyana A.,Shcherbinin, Vitaly A.,Trushkov, Igor V.,Cheshkov, Dmitry A.,Krapivin, Gennady D.
experimental part
p. 3316 - 3327
(2010/08/21)

Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions
(Chemical Equation Presented) The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis involving well-defined gold species.
Ramon, Ruben S.,Bosson, Johann,Diez-Gonzalez, Silvia,Marion, Nicolas,Nolan, Steven P.
experimental part
p. 1197 - 1202
(2010/04/02)

Gold Activation of Nitriles: Catalytic Hydration to Amides
A gold-based catalytic system that efficiently mediates the hydration of a broad spectrum of nitriles, including aromatic, heteroaromatic and aliphatic examples and efficiently catalyze the hydration of a range of organonitriles has been reported. Nitriles are considered inert in the context gold catalysis and have only been used as reaction solvent or as throw-away ligands in well-defined cationic gold catalysis. The obtained product was purified by flash chromatography using a gradient of pentane/ethyl acetate and compound 1 was isolated as a colorless solid. Aromatic substrates bearing two nitrile groups as in rn-benzenedinitrile and p-benzenedinitrile underwent double nitrile hydration and afforded excellent yields in the corresponding diamides. There is high relevance for the use of cationic gold complexes bearing such ligands and should have important implications in catalysis.
Ramon, Ruben S.,Marion, Nicolas,Nolan, Steven P.
supporting information; experimental part
p. 8695 - 8697
(2010/03/24)

AMIDE DERIVATIVES AS SIRTUIN MODULATORS
Provided herein are novel sirtuin-modulating compounds represented by Structural Formula (I) and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin- modulating compound in combination with another therapeutic agent.
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(2009/06/27)

Highly efficient ruthenium-catalyzed oxime to amide rearrangement
A wide range of aldoximes has been converted into the corresponding amides using the ruthenium-based catalyst Ru(PPh3)3(CO)H 2/dppe/ TsOH. The amides are generated in high yield and selectivity, with catalyst loading as low as 0.04 mol %.
Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
p. 3599 - 3601
(2008/02/12)

A facile hydration of nitriles into amides by Al2O3/MeSO3H (AMA)
A new and practical method for the conversion of nitriles to amides by employing the A12O3/MeSO3H (AMA) is described.
Sharghi, Hashem,Sarvari, Mona Hosseini
p. 207 - 212
(2007/10/03)