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

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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.

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Authors and Affiliations

  1. Voronezh State University, Universitetskaya pl. 1, Voronezh, 394006, Russia

    I. V. Ledenyova, A. V. Falaleev & Kh. S. Shikhaliev

  2. Peoples’ Friendship University of Russia, ul. Miklukho-Maklaya 6, Moscow, 117198, Russia

    E. A. Ryzhkova & F. I. Zubkov

Authors
  1. I. V. Ledenyova
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  2. A. V. Falaleev
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  3. Kh. S. Shikhaliev
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  4. E. A. Ryzhkova
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  5. F. I. Zubkov
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Correspondence to I. V. Ledenyova.

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Original Russian Text © I.V. Ledenyova, A.V. Falaleev, Kh.S. Shikhaliev, E.A. Ryzhkova, F.I. Zubkov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 1, pp. 77–83.

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Ledenyova, I.V., Falaleev, A.V., Shikhaliev, K.S. et al. Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism. Russ J Gen Chem 88, 73–79 (2018). https://doi.org/10.1134/S1070363218010115

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  • DOI: https://doi.org/10.1134/S1070363218010115

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