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A convenient synthesis method of 5-oxopyrazolo[4,3-b]pyridine-6-carboxylic acids and their nitriles

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Chemistry of Heterocyclic Compounds Aims and scope

N-Boc-protected 5-formyl-1H-pyrazol-4-amines react with malonic acid in pyridine in the presence of pyrrolidine at 45–50°С or with malonic acid monomethyl ether in the presence of pyrrolidine in AcOH under reflux with the formation of 5-oxo-4,5-dihydro-1Hpyrazolo[4,3-b]pyridine-6-carboxylic acids. The reaction of N-Boc-protected 5-formyl-1H-pyrazol-4-amines with cyanoacetic acid in pyridine in the presence of pyrrolidine at 45–50°С leads to the formation of 5-oxo-4,5-dihydro-1H-pyrazolo[4,3-b]pyridine-6-carbonitriles. The latter can also be obtained via cyclocondensation of N-Boc-protected 5-formyl-1H-pyrazol-4-amines with methyl cyanoacetate in AcOH under reflux in the presence of pyrrolidine or in MeCN containing pyrrolidine and a catalytic amount of proline heated under reflux.

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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, 02094, Ukraine

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

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

    Andriy V. Bol’but

Authors
  1. Georgiy G. Yakovenko
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  2. Oleh А. Lukianov
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  3. Andriy V. Bol’but
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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, 2019, 55(12), 1211–1216

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Yakovenko, G.G., Lukianov, O.А., Bol’but, A.V. et al. A convenient synthesis method of 5-oxopyrazolo[4,3-b]pyridine-6-carboxylic acids and their nitriles. Chem Heterocycl Comp 55, 1211–1216 (2019). https://doi.org/10.1007/s10593-019-02603-5

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  • DOI: https://doi.org/10.1007/s10593-019-02603-5

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