The reaction of carbon disulfide with bromoacetophenone in the presence of primary amines: synthesis of 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives

A three-component reaction between a primary amine, carbon disulfide, and bromoacetophenone that affords novel 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives is reported. The reaction sequence consists of an initial nucleophilic addition of primary amines to carbon disulfide, followed by the nucleophilic attack of carbamodithioic acid so obtained to the bromoacetophenone, and then ring closure by intramolecular attack of nitrogen to the carbonyl carbon to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described molecules that have biological specifications. [GRAPHICS] .