Thiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. Using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of adducts was demonstrated by hydrolysis, amidation and oxidation reactions.
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