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
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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.
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proposed mechanism
Key Words
benzisothiazol-3-ones, oxygen, benzo-fused N-heterocycles, benzo-fused S-heterocycles
ID: J42-Y2023