Email this article Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism
- Authors: Ledenyova I.V.1, Falaleev A.V.1, Shikhaliev K.S.1, Ryzhkova E.A.2, Zubkov F.I.2
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Affiliations:
- Voronezh State University
- Peoples’ Friendship University of Russia
- Issue: Vol 88, No 1 (2018)
- Pages: 73-79
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221946
- DOI: https://doi.org/10.1134/S1070363218010115
- ID: 221946
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Abstract
The reaction of ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo[5,1-c][1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS.
About the authors
I. V. Ledenyova
Voronezh State University
Author for correspondence.
Email: irairachem@yandex.ru
Russian Federation, Universitetskaya pl. 1, Voronezh, 394006
A. V. Falaleev
Voronezh State University
Email: irairachem@yandex.ru
Russian Federation, Universitetskaya pl. 1, Voronezh, 394006
Kh. S. Shikhaliev
Voronezh State University
Email: irairachem@yandex.ru
Russian Federation, Universitetskaya pl. 1, Voronezh, 394006
E. A. Ryzhkova
Peoples’ Friendship University of Russia
Email: irairachem@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 6, Moscow, 117198
F. I. Zubkov
Peoples’ Friendship University of Russia
Email: irairachem@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 6, Moscow, 117198
