Organic Chemistry Portal

Abstracts

Search:

Chemodivergent Synthesis of Benzothiadiazin-3-one 1-Oxides and Benzisothiazol-3-ones via Visible Light-Promoted Intramolecular N-S Bond Formation

Huimin Li, Zhiqiang Xiong, Shouri Sheng, Junmin Chen*

*College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, Jiangxi, China, Email: junminchenjxnu.edu.cn

H. Li, Z. Xiong, S. Sheng, J. Chen, J. Org. Chem., 2023, 88, 16949-16959.

DOI: 10.1021/acs.joc.3c01775


see article for more reactions

Abstract

While an N-S bond coupling/oxidation cascade of N-(2-mercaptophenyl)-N'-substituted ureas provides benzothiadiazin-3-one 1-oxides; the transformation of 2-mercaptobenzamides only occurs via N-S bond coupling to access benzisothiazol-3-ones in good yields. The photochemical syntheses offer mild conditions, excellent chemoselectivity, and functional group compatibility.


see article for more examples

proposed mechanism



Key Words

benzisothiazol-3-ones, oxygen, benzo-fused N-heterocycles, benzo-fused S-heterocycles


ID: J42-Y2023