66749-85-7Relevant academic research and scientific papers
Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
supporting information, p. 8411 - 8422 (2019/05/17)
An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines
Benitez-Medina, G. Eliad,Ortiz-Soto, Sofía,Cabrera, Armando,Amézquita-Valencia, Manuel
, p. 3763 - 3770 (2019/06/24)
A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.
Copper-catalyzed oxidative cross-coupling of α-aminocarbonyl compounds with primary amines toward 2-oxo-acetamidines
Chen, Chuang,Zhu, Menghua,Jiang, Lihui,Zeng, Zebing,Yi, Niannian,Xiang, Jiannan
, p. 8134 - 8139 (2017/10/10)
A general and mild method for the construction of a carbon-nitrogen bond via copper-catalyzed oxidative cross-coupling of amines with α-aminocarbonyl compounds was achieved. Amines, either aliphatic primary amines, aromatic primary amines or secondary amines can be used as the starting materials. When R2 was different from R3, two isomers would be observed. Therefore, this reaction system has a broad substrate scope and provides a facile pathway for the synthesis of 2-oxo-acetamidines.
One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines
Martinez-Ariza, Guillermo,McConnell, Nicholas,Hulme, Christopher
supporting information, p. 1864 - 1867 (2016/05/19)
A cesium carbonate promoted three-component reaction of N-H containing heterocycles, primary or secondary amines, arylglyoxaldehydes, and anilines is reported. The key step involves a tandem sequence of N-1 addition of a heterocycle or an amine to preform
Copper-Catalyzed C?N Bond Formation via Oxidative Cross-Coupling of Amines with α-Aminocarbonyl Compounds
Liu, Xing-Xing,Wu, Zhao-Yang,He, Yong-Qin,Zhou, Xiao-Qiang,Hu, Ting,Ma, Chao-Wei,Huang, Guo-Sheng
, p. 2385 - 2391 (2016/08/16)
A novel and selective method for the simple copper-catalyzed α-amination of α-aminocarbonyl compounds to afford 2-amino-2-iminocarbonyl and 2-amino-2-oxocarbonyl compounds is reported. This transformation is achieved by C(sp3)?H and N?H bond ox
Reductive Alkylation of α-Keto Imines Catalyzed by PTSA/FeCl3: Synthesis of Indoles and 2,3′-Biindoles
Naidu, P. Seetham,Kolita, Sinki,Sharma, Meenakshi,Bhuyan, Pulak J.
, p. 6381 - 6390 (2015/06/30)
A simple and efficient method for the synthesis of highly functionalized indoles and biindoles was developed. In the reaction protocol, three components were used in one pot and products were obtained in high yield in an easy workup procedure. The reactio
α-Carbonylimine to α-Carbonylamide: An efficient oxidative amidation approach
Padala, Anil K.,Mupparapu, Nagaraju,Singh, Deepika,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 3577 - 3586 (2015/06/08)
Abstract Our interest in generating amide bonds by employing the activated C=N system has led to the development of an efficient oxidative amidation reaction between 2-oxoaldehyde and weak nucleophilic amines (anilines, benzamides and sulfonamides). Mechanistic studies support the involvement of α-carbonylimine (-CO-C=N-) based compounds or intermediates as a central feature of the reaction, in which an adjacent CO moiety enhances the electrophilicity of the C=N system, which favors attack of the oxidant (TBHP or SeO2), thereby resulting in the generation of the desired products in good yields. The direct oxidative coupling of 2-oxoaldehydes and weak nucleophilic amines has been accomplished through either MgSO4-TBHP-pyridine/CuBr, or SeO2·pyridine promoted methods. In the current study, SeO2·pyridine emerged as a versatile reagent with which to promote initial α-carbonylimine formation between 2-oxoaldehyde and weak nucleophilic amine, and subsequent oxidation to the corresponding α-carbonylamide. The reported methodology constitutes one of the few reports of the synthesis of α-ketoamides from anilines, perhaps the second report for the generation of α-ketoimides, and the first report of the generation of 2-oxoamides with sulfonamides.
Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: A simple and efficient synthesis of -ketothioamides
Eftekhari-Sis, Bagher,Vahdati-Khajeh, Saleh,Amini, S. Motahhareh,Zirak, Maryam,Saraei, Mahnaz
, p. 464 - 473 (2013/10/21)
A simple and efficient method for the synthesis of -ketothioamides via the Willgerodt-Kindler reaction is developed. Reactions were carried out between arylglyoxal hydrates, amines and elemental sulfur in water at 80°C to afford corresponding -ketothioamides in good to high yields in a short reaction time.
A mild, selective copper-catalyzed oxidative phosphonation of α-amino ketones
Yang, Bin,Yang, Ting-Ting,Li, Xi-An,Wang, Jun-Jiao,Yang, Shang-Dong
, p. 5024 - 5027 (2013/10/22)
A novel and selective method of simple copper-salt catalyzed phosphonation of α-amino carbonyl compounds to afford imidoylphosphonates is reported. This reaction system has a broad reaction scope. The convenient and environmentally benign process makes th
Antifungal activities of ketoazomethines of phenyl glyoxal and p-substituted anilines
Vats, Vishnu,Upadhyay,Sharma, Prathibha
experimental part, p. 59 - 62 (2012/02/15)
A new series of ketoazomethines were synthesized by condensation of phenyl glyoxal (prepared by partial oxidation of acetophenone) with various p-substituted anilines viz. p-Cl, p-Br, p-NO2, p-(C2H 5)2N and p-CH
