Synthesis of 1,3-Thiazolidin-4-Ones; Reactivity of the Thiosemicarbazone Function towards Dimethyl Acetylenedicarboxylate

Author:

Hassan Alaa A.1,Mohamed Shaaban K.12,Mohamed Nasr K.1,El-Shaieb Kamal M.1,Abdel-Aziz Ahmed T.1,Mague Joel T.3,Akkurt Mehmet4

Affiliation:

1. Chemistry Department, Faculty of Science, Minia University, El-Minia 61519, Egypt

2. Faculty of Science & Engineering, Manchester, Metropolitan University, Manchester M15GD, UK

3. Department of Chemistry, Tulane University, New Orleans, LA 70118, USA

4. Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey

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.

Publisher

SAGE Publications

Subject

General Chemistry

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