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A Beckmann rearrangement initiated by trifluoromethanesulfonic anhydride in the synthesis of compounds containing a new pyrazolo[3',4':5,6]pyrido[3,2-b]azepine heterocyclic system

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Chemistry of Heterocyclic Compounds Aims and scope

N-Boc-5-formylpyrazol-4-amines reacted with 1,3-cyclohexanediones in AcOH–1,4-dioxane medium in the presence of pyrrolidine, resulting in the formation of pyrazolo[4,3-b]quinolin-8-one derivatives that were converted into the respective oximes. A reaction of the latter with trifluoromethanesulfonic anhydride under mild conditions was used to synthesize hexahydropyrazolo[3',4':5,6]pyrido[3,2-b]-azepin-4-ium trifluoromethanesulfonates.

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Authors and Affiliations

  1. National University “Kyiv-Mohyla Academy”, 2 Hryhorija Skovorody St, Kyiv, 04655, Ukraine

    Georgiy G. Yakovenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St, Kyiv, 02094, Ukraine

    Georgiy G. Yakovenko, Marta S. Yagodkina-Yakovenko, Sergey Yu. Suykov & Mikhailo V. Vovk

  3. Enamine Ltd., 78 Chervonotkatska St, Kyiv, 02094, Ukraine

    Marta S. Yagodkina-Yakovenko

Authors
  1. Georgiy G. Yakovenko
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  2. Marta S. Yagodkina-Yakovenko
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  3. Sergey Yu. Suykov
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  4. Mikhailo V. Vovk
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Correspondence to Georgiy G. Yakovenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(2), 199–206

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Yakovenko, G.G., Yagodkina-Yakovenko, M.S., Suykov, S.Y. et al. A Beckmann rearrangement initiated by trifluoromethanesulfonic anhydride in the synthesis of compounds containing a new pyrazolo[3',4':5,6]pyrido[3,2-b]azepine heterocyclic system. Chem Heterocycl Comp 57, 199–206 (2021). https://doi.org/10.1007/s10593-021-02893-8

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  • DOI: https://doi.org/10.1007/s10593-021-02893-8

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