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Synthesis and photolysis of 3-tert-butyl-4-oxy(mercapto)-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines

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Abstract

Reactions of 3-tert-butyl- or 3,4-di-tert-butyl-substituted 8-methylpyrazolo[5,1-c][1,2,4]-triazines with trifluoroacetic anhydride afforded 1-(2,2,2-trifluoroacetyl)-1,4-dihydropyrazolo-[5,1-c][1,2,4]triazin-4-yl 2,2,2-trifluoroacetates. The treatment with H2X and RXH (X = O or S; R = Me or Et) of covalent trifluoroacetate that does not contain the But group at the C(4) atom allowed us to synthesize 1-(3-tert-butyl-4-R-pyrazolo[5,1-c][1,2,4]triazin-1(4H)-yl)-2,2,2-trifluoroethan-1-ones. The structure of 4-ethylthio derivative was fully established by the single-crystal X-ray diffraction analysis. The UV irradiation of obtained 2,2,2-trifluoroethan-1-ones leads to the aromatization of triazine ring. The UV photolysis of 1-trifluoroacetyl-4-hydroxy derivative has been proposed as a novel method for the photogeneration of acidity. Antimicrobial and antifungal activities of the synthesized compounds were evaluated.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    S. M. Ivanov

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    S. M. Ivanov & V. F. Traven

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. A. Lyssenko

  4. M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    K. A. Lyssenko

Authors
  1. S. M. Ivanov
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  2. K. A. Lyssenko
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  3. V. F. Traven
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Corresponding author

Correspondence to S. M. Ivanov.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (project No. 18-33-00019 mol_a; S. M. Ivanov, in the parts of synthesis and biological activity) and the Russian Science Foundation (project No. 17-13-01302; V. F. Traven, in the parts of photolysis and UV spectroscopy).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0731–0738, April, 2020.

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Ivanov, S.M., Lyssenko, K.A. & Traven, V.F. Synthesis and photolysis of 3-tert-butyl-4-oxy(mercapto)-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines. Russ Chem Bull 69, 731–738 (2020). https://doi.org/10.1007/s11172-020-2825-4

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  • DOI: https://doi.org/10.1007/s11172-020-2825-4

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