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One-pot synthesis of 5-fluoroalkyl-5-hydroxy-4-hydroxy-imino-1-isonicotinoyl-4,5-dihydro-1H-pyrazoles and their tuberculostatic activity

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Abstract

5-Fluoroalkyl-5-hydroxy-4-hydroxyimino-1-isonicotinoyl-4,5-dihydro-1H-pyrazoles were synthesized via a one-pot procedure from polyfluoroalkyl-containing 1,3-diketones, sodium nitrite in acetic acid, and isoniazid. Acetylacetone gave rise to 3-hydroxyiminopentane-2,4-dione monoisonicotinoylhydrazone which underwent intramolecular cyclization to 5-hydroxy-4-hydroxyimino-1-isonicotinoyl-3,5-dimethyl-4,5-dihydro-1H-pyrazole on heating in ethanol. The synthesized compounds exhibited moderate tuberculostatic activity.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. Akademicheskaya/S. Kovalevskoi 22/20, Yekaterinburg, 620990, Russia

    O. G. Khudina & V. I. Saloutin

  2. Federal State Enterprise “Ural Research Institute of Phthisiopulmonology, Russian Medical Technologies,”, Yekaterinburg, Russia

    Ya. V. Burgart & M. A. Kravchenko

Authors
  1. O. G. Khudina
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  2. Ya. V. Burgart
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  3. V. I. Saloutin
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  4. M. A. Kravchenko
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Corresponding author

Correspondence to V. I. Saloutin.

Additional information

Original Russian Text © O.G. Khudina, Ya.V. Burgart, V.I. Saloutin, M.A. Kravchenko, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 887–892.

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Khudina, O.G., Burgart, Y.V., Saloutin, V.I. et al. One-pot synthesis of 5-fluoroalkyl-5-hydroxy-4-hydroxy-imino-1-isonicotinoyl-4,5-dihydro-1H-pyrazoles and their tuberculostatic activity. Russ J Org Chem 47, 904–909 (2011). https://doi.org/10.1134/S1070428011060121

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  • DOI: https://doi.org/10.1134/S1070428011060121

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