A Facile Method for the Synthesis of Hydrazine-4-oxothiazolidine and Imino-5-oxothiadiazine Derivatives from 1,4-Disubstituted Thiosemicarbazides

1,4‐Disubstituted thiosemicarbazides reacted with dimethyl acetylenedicarboxylate with formation of (2‐hydrazono‐4‐oxothiazolidin‐5‐ylidene)acetates and, in one case, a (2‐imino‐1,3,4‐thiadiazin‐5‐on‐6‐ylidene)acetate. Several mechanistic options involving nucleophilic interaction are presented. The...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2014-01, Vol.51 (1), p.44-49
Main Authors: Hassan, Alaa A., Aly, Ashraf A., Bedair, Tarek I. M., Brown, Alan B., El-Emary, Talaat I.
Format: Article
Language:English
Subjects:
1,4‐Disubstituted thiosemicarbazides
4-Disubstituted thiosemicarbazides
dimethyl acetylenedicarboxylate
Thiazolidinone and thiadiazinone derivatives
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Summary:1,4‐Disubstituted thiosemicarbazides reacted with dimethyl acetylenedicarboxylate with formation of (2‐hydrazono‐4‐oxothiazolidin‐5‐ylidene)acetates and, in one case, a (2‐imino‐1,3,4‐thiadiazin‐5‐on‐6‐ylidene)acetate. Several mechanistic options involving nucleophilic interaction are presented. The structures of all newly synthesized compounds were identified by 1H NMR, 13C NMR, COSY, HMQC and HMBC spectral data.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1655