The Silane-Promoted Cycloaddition of Thiobenzhydrazide with Carbon Dioxide toward 1,3,4-Thiadiazol-2(3H)-one

Abstract

Herein, we developed a silane-promoted cycloaddition of thiobenzhydrazides with carbon dioxide leading to 1,3,4-thiadiazol-2(3H)-ones. This procedure proceeds with the sequential N-silylation, and fixation of carbon dioxide toward hydrazine formyl intermediate, followed by intramolecular nucleophilic cyclization and aromatization. A series of functional groups tolerate well under this procedure. As such, it represents a facile and efficient pathway in utilizing carbon dioxide in the construction of value-added heterocyclic frameworks.