Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano-and thioamide groups, and 3,5diaminopyrazoles 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-4thiocarbamoyl 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.

Automated summary

It was found that the reaction between 2-cyanothioacetamides and hydrazine involves both cyano and thioamide groups, resulting in the formation of 3,5-diaminopyrazoles. Meanwhile, in the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, cyano and enamine groups participate in the reaction without affecting the thiocarbamoyl group, leading to the synthesis of 4-thiocarbamoylpyrazoles. A synthesis method for 1-substituted-4-thiocarbamoyl pyrazoles has been developed, and the structure of the reaction products has been confirmed using NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis.