Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate

Author:

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

Abstract

AbstractA 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.

Publisher

Springer Science and Business Media LLC

Subject

Materials Chemistry,Industrial and Manufacturing Engineering,General Chemical Engineering,Biochemistry,General Chemistry

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