Synthesis 2014; 46(22): 3097-3102
DOI: 10.1055/s-0034-1378551
paper
© Georg Thieme Verlag Stuttgart · New York

Reactions of Dimethyl Acetylenedicarboxylate with 2,5-Dithiobiurea Derivatives

Alaa A. Hassan*
a  Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Nasr K. Mohamed
a  Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Maysa M. Makhlouf
a  Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt   Fax: +20(86)236011   Email: alaahassan2001@mu.edu.eg
,
Stefan Bräse
b  Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
,
Martin Nieger
c  Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 Helsinki, Finland
› Author Affiliations
Further Information

Publication History

Received: 22 April 2014

Accepted after revision: 01 July 2014

Publication Date:
14 August 2014 (eFirst)

Abstract

Symmetrically and unsymmetrically N1,N2-disubstituted hydrazine-1,2-dicarbothioamides (2,5-dithiobiureas) react with dimethyl acetylenedicarboxylate in refluxing ethanol to give dimethyl 2,2′-[2,2′-(hydrazine-1,2-diylidene)bis(3-aryl/alkyl-4-oxothiazolidine-5,2-diylidene)diacetate and methyl 2-(2-{[5-(2-methoxy-2-oxoethylidene)-4-oxothiazolidin-2-ylidene]hydrazono}-4-oxothiazolidin-5-ylidene)acetate derivatives and N2,N5-disubstituted 1,3,4-thiadiazole-2,5-diamines. The structure of one product has been confirmed by a single-crystal X-ray structure analysis. A rationale for the formation of the products is presented.

Supporting Information

 
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