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Synthesis and oxidation of all isomeric 2-(pyrazolyl)ethanols

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient approach to the preparation of N-substituted 2-(pyrazol-4-yl)ethanols based on recyclization reaction of 3-(dimethoxymethyl)-2-methoxytetrahydrofuran with hydrazines is described. Oxidation by KMnO4 led to 2-(pyrazol-4-yl)-2-oxoacetic acids. In contrast, 2-(pyrazol-5-yl)ethanol under similar conditions gave only pyrazole-5-carboxylic acid, which formed as a result of oxidation followed by decarbonylation. 2-(Pyrazol-3-yl)ethanol in this oxidation reaction gave a mixture of 2-oxo-2-(pyrazol-3-yl)acetic acid and pyrazole-3-carboxylic acid.

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Authors and Affiliations

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

    Sergey P. Ivonin, Eduard B. Rusanov & Dmitriy M. Volochnyuk

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

    Dmitriy M. Volochnyuk

  3. Taras Shevchenko National University of Kyiv, 60 Volodymyrska St, Kyiv, 01601, Ukraine

    Dmitriy M. Volochnyuk

Authors
  1. Sergey P. Ivonin
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  2. Eduard B. Rusanov
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  3. Dmitriy M. Volochnyuk
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Correspondence to Dmitriy M. Volochnyuk.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 320–325

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Ivonin, S.P., Rusanov, E.B. & Volochnyuk, D.M. Synthesis and oxidation of all isomeric 2-(pyrazolyl)ethanols. Chem Heterocycl Comp 56, 320–325 (2020). https://doi.org/10.1007/s10593-020-02662-z

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  • DOI: https://doi.org/10.1007/s10593-020-02662-z

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