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

Hassan, Alaa; Mohamed, Shaaban; Mohamed, Nasr; El-Shaieb, Kamal; Abdel-Aziz, Ahmed; Mague, Joel; AKKURT, MEHMET

doi:10.3184/174751916x14552868764580

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, Scopus)

Publication Type: Article / Article
Publication Date: 2016
Doi Number: 10.3184/174751916x14552868764580
Journal Name: JOURNAL OF CHEMICAL RESEARCH
Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Page Numbers: pp.173-177
Erciyes University Affiliated: Yes

Abstract

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.