Issue 37, 2023

Construction of benzoheterocycles by the reaction of α-arylglyoxylic acids and ortho-functionalized aniline under mild and minimal conditions

Abstract

This work describes an environmentally friendly method for the synthesis of benzoxazinones, quinoxalinones and benzothiazoles by the reaction of α-arylglyoxylic acids and ortho-functionalized aniline. In this reaction, no other reagents are needed except for reactants and solvents. The reaction was carried out at a mild temperature of 50 °C with only water and/or carbon dioxide as the by-product. Therefore, the reaction has high practical atom economy. In addition, this strategy could be scaled up to the gram level, and the natural product Cephamandole A could be synthesized on a mass scale.

Graphical abstract: Construction of benzoheterocycles by the reaction of α-arylglyoxylic acids and ortho-functionalized aniline under mild and minimal conditions

Supplementary files

Article information

Article type
Paper
Submitted
22 Jul 2023
Accepted
18 Aug 2023
First published
08 Sep 2023

Org. Biomol. Chem., 2023,21, 7639-7642

Construction of benzoheterocycles by the reaction of α-arylglyoxylic acids and ortho-functionalized aniline under mild and minimal conditions

H. Gong, F. Zhou and C. Cai, Org. Biomol. Chem., 2023, 21, 7639 DOI: 10.1039/D3OB01163A

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