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Rearrangement of thiazolo[3,2-a]pyrimidines into triazolo[4,3-a]pyrimidines induced by C=N bond reduction

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Chemistry of Heterocyclic Compounds Aims and scope

Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]- pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)- 5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data. The mechanism of the reaction including transition cage structure is discussed.

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This work was financially supported by the Ministry of Science and High Education of the Russian Federation as a basic part of a research project (4.6764.2017/BP).

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russia

    Eugenia A. Lashmanova, Artem S. Agarkov & Andrey K. Shiryaev

  2. Moscow M. V. Lomonosov State University, 1 Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Victor B. Rybakov

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  1. Eugenia A. Lashmanova
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  2. Artem S. Agarkov
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  3. Victor B. Rybakov
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  4. Andrey K. Shiryaev
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Correspondence to Andrey K. Shiryaev.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(12), 1217–1221

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Lashmanova, E.A., Agarkov, A.S., Rybakov, V.B. et al. Rearrangement of thiazolo[3,2-a]pyrimidines into triazolo[4,3-a]pyrimidines induced by C=N bond reduction. Chem Heterocycl Comp 55, 1217–1221 (2019). https://doi.org/10.1007/s10593-019-02604-4

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  • DOI: https://doi.org/10.1007/s10593-019-02604-4

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