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One-Pot Domino Reaction: Direct Access to Polysubstituted 1,4-Benzothiazine 1,1-Dioxide via Water-Gas Shift Reaction Utilizing DMF/H2O

Yogesh Sharma, Ganesh P. Pawar and Vinod D. Chaudhari*

*Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India, Email:

Y. Sharma, G. P. Pawar, V. D. Chaudhari, J. Org. Chem., 2023, 88, 701-710.

DOI: 10.1021/acs.joc.2c02171

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A water-gas shift reaction (WGSR) employing sodium 2-nitrobenzenesulfinates and α-bromo ketones enables a facile domino approach to benzothiazine 1,1-dioxides. This strategy is cost-effective and environmentally beneficial. The optimized reaction conditions demonstrated remarkable chemical tolerance to a wide range of electrically and sterically varied substituents on both coupling partners.

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proposed mechanism

Key Words

benzo-fused N-heterocycles, benzo-fused S-heterocycles

ID: J42-Y2023