Reactions of α-Phenylglyoxylic Acids with ortho-Functionalized Anilines in Deep Eutectic Solvents: Selective Syntheses of 3-Aryl-2H-benzo[b][1,4]oxazin-2-ones, 2-Arylbenzothiazoles, and 3-Arylquinoxalin-2(1H)-ones

Guofang Jiang, Guoqing Chen, Jiangnan Yang, Hongxia Li, Zhongsheng Chen, Zongbo Xie*, Zhanggao Le*

*Qujing Normal University, Qujing, 655011; Yunnan Minzu University, Kunming, 650500, P. R. of China, Email: zbxieecut.edu.cn, zhgleecut.edu.cn

G. Jiang, G. Chen, J. Yang, H. Li, Z. Chen, Z. Xie, Z. Le, Synthesis, 2022, 54, 3069-3076.

DOI: 10.1055/a-1780-1691

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Abstract

Cyclizations of α-phenylglyoxylic acids with ortho-functionalized anilines in deep eutectic solvents (DES) provide 2-arylbenzothiazoles (from o-aminothiophenols), 3-aryl-2H-benzo[b][1,4]oxazin-2-ones (from o-aminophenols), and 3-arylquinoxalin-2(1H)-ones (from o-phenylenediamines) without the addition of other catalysts. The title compounds were obtained in good yields under mild conditions.

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Key Words

2-benzoxazinones, selective cyclization reaction, deep eutectic solvent, α-phenylglyoxylic acids, ortho-functionalized anilines

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ID: J66-Y2022