A Novel Synthetic Approach to Benzo[d]isothiazole 1,1‐Diones Having a Secondary Alkyl Substituent at the 3‐Position

Abstract

A novel method for the synthesis of benzo[d]isothiazole 1,1‐diones with a secondary alkyl substituent at the 3‐position is described. Treatment of N‐tert‐butylbenzenesulfonamide (1) with an excess of BuLi, followed by the reaction with methyl 2‐arylpropanoate, gave the corresponding ortho‐functionalized benzenesulfonamides 2a–d, which underwent cyclization under TMSCl–NaI–MeCN reflux conditions to afford 3‐substituted benzo[d]isothiazole 1,1‐diones 3a–d.

Keywords:

• Benzo[d]isothiazole 1,1‐diones
• N‐tert‐butylbenzene‐sulfonamide
• Methyl 2‐arylpropanoate
• TMSCl–NaI–MeCN