Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

Autor: Valeriy O. Filimonov, Alexandra I. Topchiy, Vladimir G. Ilkin, Tetyana V. Beryozkina, Vasiliy A. Bakulev
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 19, Iss 1, Pp 1191-1197 (2023)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.19.87
Popis: It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano- and thioamide groups, and 3,5-diaminopyrazoles are formed. In the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, the interaction proceeds with the participation of cyano- and enamine groups, not affecting the thiocarbamoyl group, and leads to the formation of 4-thiocarbamoylpyrazoles. A synthesis method has been developed and a series of 1-substituted-4-thiocarbamoyl pyrazoles has been thus synthesized. The structure of the reaction products was studied using NMR spectroscopy and mass spectrometry and confirmed by X-ray diffraction analysis.
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