Efficient synthesis of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters

Abstract

Efficient methods for the preparation of polyfunctionalized thiophene-2,3-diones and thiophen-3(2H)-ones using β-oxodithioesters were described. In this study, β-oxodithioesters were found to react directly with oxalyl chloride producing 4-aroyl-5-(methylthio)thiophene-2,3-diones in 96–98% yields. However, β-oxodithioesters were found to react efficiently with chloroacetic anhydride in the presence of a base catalyst such as DMAP, which gave 4-aroyl-5-(methylthio)thiophen-3(2H)-ones in 61–77% yields.