Chemoselective synthesis of aryl carboxamido sulfonic acid derivatives

Abstract

A one-pot two-step synthetic strategy for the preparation of aryl carboxamido sulfonic acid derivatives was developed. The synthesis started from m-(chlorosulfonyl)benzoyl chloride, which was reacted with amines, alcohols, thiols, or sodium azide and catalytic activator at rt to give the corresponding sulfonic acid derivatives in good yields. The short reaction times and the one-pot chemoselective nature of the procedure diminished undesired side reactions and enhanced the efficiency of the reaction. In cases of electron-donor and electron-deficient substituted carboxanilides, piperidine was successfully incorporated at sulfur to obtain the corresponding sulfonamides in yields of 46% (4-nitroaniline) to nearly quantitative (4-methoxyaniline). The optimized conditions were applied to the preparation of diarylsulfonamides, sulfonic esters, thiosulfonates, and a sulfonyl azide, which are very important and key structures in modern organic synthesis. Furthermore, the method has been successfully used in the preparation of inhibitors of isocitrate dehydrogenase mutants, which are closely related to tumorigenesis.