Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism

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. © 2018, Pleiades Publishing, Ltd.

Authors
Ledenyova I.V.1 , Falaleev A.V.1 , Shikhaliev K.S.1 , Ryzhkova E.A. 2 , Zubkov F.I. 2
Number of issue
1
Language
English
Pages
73-79
Status
Published
Volume
88
Year
2018
Organizations
  • 1 Voronezh State University, Universitetskaya pl. 1, Voronezh, 394006, Russian Federation
  • 2 Peoples’ Friendship University of Russia, ul. Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
Keywords
ANRORC rearrangement; ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylate; formylation; thiourea
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/7050/
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