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Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives.

Valeriy O FilimonovAlexandra I TopchiyVladimir G IlkinTetyana V BeryozkinaVasiliy A Bakulev
Published in: Beilstein journal of organic chemistry (2023)
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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