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Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines

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Chemistry of Heterocyclic Compounds Aims and scope

Rearrangements of 3-tert-butyl-8-methyl-4-phenylethynyl-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine derivatives by the action of bases led to the formation of aromatic (E)- or (Z)-4-styryl-functionalized compounds. At the same time, 4-styryl-1,4-dihydropyrazolotriazines did not rearrange to form the expected 4-phenylethylpyrazolo[5,1-c][1,2,4]triazine. The latter was obtained via an alternative route by the addition reaction of phenylethynylmagnesium bromide to 3-tert-butyl-8-methylpyrazolo[5,1-c][1,2,4]triazine, as well as by reduction of double bonds in the ring and side chain of the 4-styryl derivative with subsequent selective oxidation by N-bromosuccinimide. The spectral and X-ray structural data as well as the antimicrobial properties of the synthesized compounds are discussed.

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Authors and Affiliations

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

    Sergey M. Ivanov & Denis S. Koltun

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  1. Sergey M. Ivanov
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  2. Denis S. Koltun
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Correspondence to Sergey M. Ivanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(6), 656–665

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Ivanov, S.M., Koltun, D.S. Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines. Chem Heterocycl Comp 57, 656–665 (2021). https://doi.org/10.1007/s10593-021-02964-w

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  • DOI: https://doi.org/10.1007/s10593-021-02964-w

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