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Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate

Alaa A. Hassan, Fathy F. Abdel-Latif, Mohamed Abdel Aziz, Sara M. Mostafa, Stefan Bräse, and Martin Nieger

Chemistry Department, Faculty of Science

 

E-mail: alaahassan2001@mu.edu.eg

Abstract: A facile and rapid procedure for the synthesis of dimethyl-2-[3-amino-5-(2-methoxy-2-oxoethylidene)- 4-oxothiazolidin-2-ylidenehydrazono]succinate, dimethyl {[2-alkylidenehydrazono)-5-(2-methoxy- 2-oxoethylidene)-4-oxothiazolidin-3-yl)amino]succinate and methyl (4-amino-5-oxo-3- thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl)acetate affording yields of 61-54 %, 22-18 % and 14- 11 %, respectively, via a condensation reaction of dimethyl acetylenedicarboxylate (DMAD) with (substituted ylidene)thiocarbonohydrazides. One of the products was conclusively confirmed by single-crystal X-ray analysis. A mechanism for the formation of the products is presented

Keywords: thiocarbonohydrazides – dimethyl acetylenedicarboxylate – hydrazonothiazolidinyl-succinates – aminothioxotriazinylacetate

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0092

 

Chemical Papers 69 (7) 973–982 (2015)

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