62103-87-1Relevant articles and documents
α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
, p. 14866 - 14882 (2021/10/25)
A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
Unexpected TFA-catalyzed tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: Synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and cephalandole A
Yan, Shaoxi,Ye, Leping,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Gao, Wenxia,Huang, Xiaobo,Wu, Huayue
, p. 16705 - 16709 (2014/05/06)
A convenient and efficient method for the TFA-catalyzed synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones via a tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids was reported for the first time. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A. Moreover, a plausible mechanism for the formation of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones involving ring-opening and cyclization steps is proposed. The present synthetic route to 3-aryl-2H-benzo[b][1,4]oxazin-2-ones could be readily scaled up to gram quantity without difficulty.