This submission belongs to the session a. General Organic Synthesis of the event The 17th International Electronic Conference on Synthetic Organic Chemistry
Published date
31 Oct, 2013
Citation
Irina Ledeneva, Vitaly Didenko, Victor V. Dotsenko, Khidmet Shikhaliev, Synthesis and reactions of pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides, in Proceedings of The 17th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2013, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-17-a040
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Synthesis and reactions of pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides
Irina Ledeneva 1
Vitaly Didenko 1
Victor V. Dotsenko 2,3,4
Khidmet Shikhaliev 1
1. Voronezh State University, 1 Universitetskaya pl., 394006 Voronezh, Russia
Cyanothioacetamide reacts with pyrazole-3(5)-diazonium chlorides under mild conditions to afford pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides. The latter can be oxidized with H2O2 to give either pyrazolo[5,1-c][1,2,4]triazine-3-carboxamides or 1,2,4-thiadiazole derivatives, depending on the reaction conditions. The Hantzsch-type reaction of thioamides 5 with α-bromo ketones leads to 3-(thiazol-2-yl)pyrazolo[5,1-c][1,2,4]triazines.
Keywords
Azo-coupling
Cyanothioacetamide
Hantzsch thiazole synthesis
Heterocyclization
Pyrazole-3(5)-diazonium salts
Pyrazolo[5,1-c][1,2,4]triazines
Oxidation of thioamides
Manuscript
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