Filimonov Valeriy O, Topchiy Alexandra I, Ilkin Vladimir G, Beryozkina Tetyana V, Bakulev Vasiliy A
Technology of Organic Synthesis Department, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st. Yekaterinburg 620002, Russia.
Department of Organic Chemistry, Perm State University, 15 Bukireva st., Perm 614990, Russia.
Beilstein J Org Chem. 2023 Aug 8;19:1191-1197. doi: 10.3762/bjoc.19.87. eCollection 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)-,-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.
结果表明，2-氰基硫代乙酰胺与肼的反应涉及氰基和硫代酰胺基团，生成3,5-二氨基吡唑。在2-氰基-3-(二甲基氨基)-α,α-二甲基丙-2-烯硫代酰胺与肼及其衍生物的反应中，相互作用是在氰基和烯胺基团参与下进行的，不影响硫代甲酰基，生成4-硫代甲酰基吡唑。已开发出一种合成方法，并据此合成了一系列1-取代-4-硫代甲酰基吡唑。利用核磁共振光谱和质谱研究了反应产物的结构，并通过X射线衍射分析进行了确证。
