Ionic Liquid-Mediated One-Pot 3-Acylimino-3H-1,2-dithiole Synthesis from Thiocarboxylic Acids and Alkynylnitriles via In Situ Generation of Disulfide Intermediates

ABSTRACT: A practical and straightforward strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This operationally simple protocol offers an easy and rapid access to a library of dithiol derivatives in moderate to good yields. The mechanistic studies show a benzoyldithio anion addition to alkynylnitriles followed by an annulation reaction through the involvement of a disulfide moiety as the key intermediate.

Automated summary

A practical strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This simple protocol offers an easy and rapid access to a library of dithiol derivatives in moderate to good yields.