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

Benzothiazine 1,1-dioxide (BTDO) is a privileged chemical motif, and its metal-free domino access is in high demand. Current BTDO production methods require costly metal catalysts or harsh reaction conditions. A facile domino approach to BTDO via a water-gas shift reaction (WGSR) employing sodium 2-nitrobenzenesulfinates and alpha-bromo ketones is presented. 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.

Automated summary

Benzothiazine 1,1-dioxide (BTDO), a privileged chemical motif, can be synthesized through a cost-effective and environmentally beneficial domino approach using a water-gas shift reaction (WGSR) with sodium 2-nitrobenzenesulfinates and alpha-bromo ketones. The optimized reaction conditions show remarkable chemical tolerance to various electronically and sterically diverse substituents on both coupling partners.