A study of the behaviour of 2,4-substituted thiosemicarbazides toward orthoesters: Formation of mesoionic compounds

The reactions beetwen 2,4‐disubstituted thiosemicarbazides and orthoesters in refluxing xylene led to the formation of the 1,2,4‐triazoline‐5‐thione ring and to the 1,2,4‐triazolium‐5‐thiolate ring. The formation of the mesoionic componds is due to rearrangement of the easily available 2,4‐disubstit...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 1997-09, Vol.34 (5), p.1447-1451
Main Authors: Buccheri, Francesco, Cusmano, Giuseppe, Gruttadauria, Michelangelo, Noto, Renato, Werber, Giuseppe
Format: Article
Language:English
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Summary:The reactions beetwen 2,4‐disubstituted thiosemicarbazides and orthoesters in refluxing xylene led to the formation of the 1,2,4‐triazoline‐5‐thione ring and to the 1,2,4‐triazolium‐5‐thiolate ring. The formation of the mesoionic componds is due to rearrangement of the easily available 2,4‐disubstituted thiosemicarbazides to 1,4‐disubstituted thiosemicarbazides under the reaction conditions adopted. This method can be usefully used for the synthesis of mesoionic compounds, especially in the case of the 2‐methyl‐4‐phenylthiosemicarbazide.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570340512