Triflic Anhydride-Promoted Cyclization of Sulfides: A Convenient Synthesis of Fused Sulfur Heterocycles

Abstract

A new approach to the synthesis of annulated sulfur heterocycles based on triflic anhydride-promoted cyclization of the hetaryl(aryl) containing alkyl sulfides was elaborated. Smooth de­methylation of initially formed cyclic sulfonium salts by treatment with triethylamine afforded a number of five-, six- and seven-membered fused sulfur heterocycles. Unexpected ring opening took place in the reaction of diethylamine with 5-membered sulfonium salts.

Key words

cyclizations - electrophilic aromatic substitutions - sulfur heterocycles - bicyclic compounds - sulfonylsulfonium salts

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