62573-86-8Relevant academic research and scientific papers
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
supporting information, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes
Chen, Ling-Yan,Wu, Mei-Fang
, p. 1595 - 1602 (2019/03/26)
An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60-96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.
Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
DIssanayake, D.M.M. Mevan,Vannucci, Aaron K.
supporting information, p. 457 - 460 (2019/01/23)
An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This "anion pool" approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles. The reaction can also be performed using a 9 V battery without loss of reaction efficiency.
A azole amide preparation method of the compound
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Paragraph 0019-0021; 0025-0027, (2018/04/27)
A preparation method of an azole-series amide compound. The invention discloses a method including a reaction that the azole-series amide is synthesized from a carboxylic acid compound and an azole compound with a copper salt as a catalyst and molecular o
Synthesis and antimicrobial activity of some benzimidazole and 2-methylbenzimidazole derivatives
Jain,Tiwari
, p. 838 - 842 (2017/02/10)
In the present work, benzimidazole and 2-methylbenzimidazole derivatives were synthesized and evaluated for antimicrobial activity against Escherichia coli (Gram-negative bacteria), Staphylococcus aureus (Gram-positive bacteria) and Candida albicans (fungal stain). The structure of the synthesized compounds was confirmed by FTIR, 1H NMR and mass spectroscopy. Antimicrobial activity of all the synthesized compounds was carried out by Broth dilution method to determine MIC value. Compounds P2, P7 and P10 showed better antibacterial activity against Escherichia coli as compared to benzimidazole, 2-methylbenzimidazole and ampicillin. Compounds P8 and P12 showed better antibacterial activity against Staphylococcus aureus as compared to benzimidazole, 2-methylmenzimidazole and ampicillin. Compound P2 and P9 showed better antifungal activity against Candida albicans as compared to benzimidazole, 2-methylbenzimidazole and griseofulvin.
Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides
Mai, Shaoyu,Zhao, Yingwei,Song, Qiuling
supporting information, p. 8685 - 8690 (2016/10/03)
C-N bond formation via a copper-catalyzed aerobic oxidative decarboxylative tandem protocol was realized. The phenylacetic acids which contain ortho-X (X = F or Br) on the aromatic ring will render a fused five-membered heterocycle via a tandem aromatic nucleophilic substitution and aerobic oxidative decarboxylative acylation at the C(sp2)-H bond of benzimidazoles under the Cu(OAc)2/K2CO3/BF3·Et2O catalytic system, while with CuBr as the catalyst and pyridine as the base, N-acylation occurred and tertiary amides were obtained.
Direct synthesis of amides from coupling of alcohols and amines catalyzed by ruthenium(II) thiocarboxamide complexes under aerobic conditions
Sindhuja, Elangovan,Ramesh, Rengan,Balaji, Sundarraman,Liu, Yu
, p. 4269 - 4278 (2014/12/09)
Four octahedral ruthenium(II) thiocarboxamide complexes of the general formula [RuClCO(AsPh3)2(L)] (L = N-substituted pyridine-2-thiocarboxamide) incorporating carbonyl and triphenylarsine have been synthesized from the reaction of 1 equiv of ruthenium precursor [RuHClCO(AsPh3)3] with 1 equiv of thiocarboxamide ligands in refluxing ethanol in the presence of base. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. Molecular structures of all the complexes were determined by X-ray crystallography, which confirm the coordination mode of thiocarboxamide and reveal the presence of a distorted octahedral geometry around the Ru ion. All the ruthenium(II) thiocarboxamide complexes were generated as highly efficient catalysts for synthesis of secondary or tertiary amides by coupling of amines and alcohols with low catalyst loading, and the maximum yield was obtained up to 97%. The coupling reaction can be readily carried out under mild aerobic conditions, and release of water is the only byproduct. Further, the effect of substituents of the ligand, solvents, reaction temperature, time, and catalyst loading on the catalytic activity of the complexes has been investigated. A plausible mechanism is proposed for the synthesis of amides via hemiaminal as intermediate through an oxidation of an alcohol to aldehyde.
Direct N-acylation of azoles via a metal-free catalyzed oxidative cross-coupling strategy
Zhao, Jingjing,Li, Pan,Xia, Chungu,Li, Fuwei
supporting information, p. 4751 - 4754 (2014/05/06)
The KI-catalyzed N-acylation of azoles via direct oxidative coupling of C-H and N-H bonds has been developed. It could be smoothly scaled up to gram synthesis of acyl azoles. The reaction occurred by the coupling of acyl radicals and azoles to form the acyl azole radical anion, followed by its further oxidation. This journal is the Partner Organisations 2014.
Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles
Yu, Lin,Wang, Min,Wang, Lei
, p. 5391 - 5397 (2015/03/30)
A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency.
Solvent free, highly chemoselective N and O-acylation on silica and silica magnesium oxide: A recyclable solid surface
Ghosh, Pranab,Mandal, Amitava
, p. 261 - 268 (2012/10/29)
Silica or silica/magnesium oxide mixed surface mediates the N and O-acylation, benzoylation or sulfonylation of hosts of substrates under solvent free conditions at ambient temperature with high chemoselectivity.
