Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• , Perm State University, 15 Bukireva st., Perm 614990, Russia 10.3762/bjoc.19.87 Abstract 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

• 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. Keywords: aminopyrazoles; 2-cyanothioacetamides; enamines; hydrazines; Introduction Compounds containing a pyrazole cycle

• first present the formation of 3,5-diaminopyrazoles by reaction of 2-cyanothioacetamides with hydrazine (Scheme 1C). Our paper also contains the data on our study of reaction of 3-amino-2-cyanoprop-2-enethioamides with phenyl- and tosylhydrazines leading to novel 3-amino-4-thiocarbamoylpyrazoles (Scheme