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Convenient Preparation of N-Acylbenzoxazines from Phenols, Nitriles, and DMSO Initiated by a Catalytic Amount of (COCl)2

Hao Wang, Zeyu Xi, Shuai Huang, Rui Ding, Yang Gao, Yongguo Liu, Baoguo Sun, Hongyu Tian* and Sen Liang*

*Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China, Email: tianhybtbu.edu.cn, liangsenbtbu.edu.cn

H. Wang, Z. Xi, S. Huang, R. Ding, Y. Gao, Y. Liu, B. Sun, H. Tian, S. Liang, J. Org. Chem., 2021, 86, 4932-4943.

DOI: 10.1021/acs.joc.0c02768 (free Supporting Information)


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Abstract

Phenols react with nitriles and dimethyl sulfoxide (DMSO) in the presence of a catalytic amount of (COCl)2 in CH3CN or chloroform to afford the corresponding N-acylbenzoxazines in good yields. DMSO acts as a source of HCHO, which is generated in situ.


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proposed mechanism



Key Words

benzo-fused N-heterocycles, benzo-fused O-heterocycles


ID: J42-Y2021