Synthesis of 1,3-thiazolidin-4-ones; reactivity of the thiosemicarbazone function towards dimethyl acetylenedicarboxylate

Hassan A. A., Mohamed S. K., Mohamed N. K., El-Shaieb K. M., Abdel-Aziz A. T., Mague J. T., ...More

JOURNAL OF CHEMICAL RESEARCH, no.3, pp.173-177, 2016 (SCI-Expanded) identifier identifier


Aryl thiosemicarbazones react rapidly in a facile procedure with dimethyl acetylene-dicarboxylate to give substituted (ylidene) hydrazono(4-oxothiazolidin-5-ylidene) acetates in high yields. The synthesised compounds were characterised by spectroscopic methods and the structures confirmed by single crystal X-ray crystallography. Several mechanistic options involving nucleophilic interaction are presented.