Cycloaddition of CS2 to N-benzylaziridine to synthesize N-benzylthiazolidine-2-thione: a novel reaction route proposed by DFT Study

摘要

N-Benzylthiazolidine-2-thione is the key intermediate for the synthesis of pharmaceutically important compounds. A novel route for the synthesis of N-benzylthiazolidine-2-thione through cycloaddition of CS2 with Nbenzylaziridine in the presence of 1,3-di-tert-butylimidazolium-2-dithocarboxylate (catalyst I) has been proposed by reliable computations performed within the formalism of density functional theory. The mechanism of the proposed reaction is similar to the cycloaddition of tertiary aziridines and carbon dioxide using a recyclable catalyst that is reported to provide access to 3-substituted 2-oxazolidones with excellent yield. Because the rate determining step needs to surmount a high energy barrier, the reaction route has been deciphered in high boiling solvent (1, 2-ethanediol). The highlight of the mechanistic route detailed here is that the proposed pathway is a cyclic process that is exothermic in nature with the regeneration of the catalyst and involves simple reagents. Copyright (C) 2016 John Wiley & Sons, Ltd.