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Synthesis of 5-amino-1H-pyrazolo[4,3-b]pyridine derivatives and annulation of imidazole and pyrimidine rings thereto

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Chemistry of Heterocyclic Compounds Aims and scope

1-Alkyl-N-Boc-5-formylpyrazol-4-amines react with malononitrile and cyanoacetamide to form 5-amino-1H-pyrazolo[4,3-b]pyridine nitriles and amides, respectively. Cyclocondensation of the obtained derivatives with chloroacetaldehyde, bromotrifluoroacetone, or ethyl bromopyruvate leads to the formation of imidazo[1,2-a]pyrazolo[3,4-e]pyridines or to pyrazolo[3′,4′,5,6]pyrido[2,3-d]pyrimidine derivatives in cyclocondensation with orthoesters, ethyl oxalyl chloride, or carbonyldiimidazole.

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Authors and Affiliations

  1. National University “Kyiv-Mohyla Academy”, 2 Hrygorija Skorovody St., Kyiv, 04655, Ukraine

    Georgiy G. Yakovenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Georgiy G. Yakovenko, Oleh А. Lukianov, Marta S. Yagodkina-Yakovenko, Andriy V. Bol’but & Mikhailo V. Vovk

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

    Andriy V. Bol’but

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  1. Georgiy G. Yakovenko
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  2. Oleh А. Lukianov
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  3. Marta S. Yagodkina-Yakovenko
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  4. Andriy V. Bol’but
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  5. Mikhailo V. Vovk
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Correspondence to Georgiy G. Yakovenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 347–354

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Yakovenko, G.G., Lukianov, O.А., Yagodkina-Yakovenko, M.S. et al. Synthesis of 5-amino-1H-pyrazolo[4,3-b]pyridine derivatives and annulation of imidazole and pyrimidine rings thereto. Chem Heterocycl Comp 56, 347–354 (2020). https://doi.org/10.1007/s10593-020-02666-9

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  • DOI: https://doi.org/10.1007/s10593-020-02666-9

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