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The Reactivity of Dimethyl Acetylenedicarboxylate and Heterocyclization of Hydrazinecarbothioamides to 1,3‐Thiazolidin‐4‐ones
Author(s) -
Hassan Alaa A.,
Mohamed Nasr K.,
ElShaieb Kamal M. A.,
Tawfeek Hendawy N.,
Bräse Stefan,
Nieger Martin
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2392
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , reactivity (psychology) , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , cycloaddition , catalysis , alternative medicine , pathology , medicine
2‐Substituted hydrazinecarbothioamides and N ,2‐disubstituted hydrazinecarbothioamides react, in high yields with dimethyl acetylenedicarboxylate to give 4‐oxo‐ Z ‐(thiazolidin‐5‐ylidene)acetate derivatives. Several mechanistic options involving interaction are presented. The structures of thiazolidin‐4‐ones have been unambiguously confirmed by single crystal X‐ray crystallography.