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Synthesis of 1-(pyrrolidin-2-ylmethyl)-1H-azoles and their piperidine-derived homologues

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Central European Journal of Chemistry

Abstract

A convenient preparation of 1-(pyrrolidin-2-yl)-1H-pyrazoles, -imidazoles, and -1H-1,2,4-triazoles, 1-(piperidin-2-yl)-1H-pyrazoles and -1H-1,2,4-triazoles, and 1-(piperidin-3-yl)-1H-1,2,4-triazoles by alkylation of azoles (viz. pyrazoles, imidazoles, and triazoles) with N-Cbz-prolinol mesylate or its analogues and subsequent deprotection is reported. The two-step method allows for synthesis of the title compounds in 16–65% yields. The utility of the procedure has been demonstrated by multigram preparation of a 15-member building block mini-library for the lead-oriented synthesis of compound libraries. These building blocks perfectly fit the definition of low-molecular-weight hydrophilic three-dimensional templates, which leave much room for the lead-oriented synthesis of the compound libraries.

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Authors and Affiliations

  1. Enamine Ltd., Kyiv, 01103, Ukraine

    Sergey Zhersh, Oleksandr V. Karpenko, Vasyl Ripenko & Andrey A. Tolmachev

  2. Department of Chemistry, Taras Shevchenko National University of Kyiv, Kyiv, 01601, Ukraine

    Sergey Zhersh, Andrey A. Tolmachev & Oleksandr O. Grygorenko

Authors
  1. Sergey Zhersh
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  2. Oleksandr V. Karpenko
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  3. Vasyl Ripenko
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  4. Andrey A. Tolmachev
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  5. Oleksandr O. Grygorenko
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Corresponding author

Correspondence to Oleksandr O. Grygorenko.

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Zhersh, S., Karpenko, O.V., Ripenko, V. et al. Synthesis of 1-(pyrrolidin-2-ylmethyl)-1H-azoles and their piperidine-derived homologues. cent.eur.j.chem. 12, 67–73 (2014). https://doi.org/10.2478/s11532-013-0344-y

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  • DOI: https://doi.org/10.2478/s11532-013-0344-y

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