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Synthesis of polyfluoroalkyl-containing 1-(4-acetoxybutyl)- and 1-(4-hydroxybutyl)pyrazoles and their tuberculostatic activity

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Abstract

Alkylation of polyfluoroalkyl-containing pyrazoles with 4-bromobutyl acetate in acetone in the presence of potassium carbonate leads to a mixture of isomeric 1-(4-acetoxybutyl)-3-fluoroalkyl- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles, which in a number of cases were successfully separated by HPLC. Deacylation in acidic medium with gaseous hydrogen chloride and in basic medium with gaseous ammonia leads to 1-(4-hydroxybutyl)pyrazoles, which manifest moderate tuberculostatic activity.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    A. E. Ivanova, O. G. Khudina, Ya. V. Burgart & V. I. Saloutin

  2. Ministry of Healthcare and Social Development of the Russian Federation, Ural Research Institute of Phthisiopulmonology, 50 ul. 22 Parts’ezda, 620039, Ekaterinburg, Russian Federation

    M. A. Kravchenko

Authors
  1. A. E. Ivanova
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  2. O. G. Khudina
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  3. Ya. V. Burgart
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  4. V. I. Saloutin
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  5. M. A. Kravchenko
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Corresponding authors

Correspondence to V. I. Saloutin or M. A. Kravchenko.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2349–2353, November, 2011.

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Ivanova, A.E., Khudina, O.G., Burgart, Y.V. et al. Synthesis of polyfluoroalkyl-containing 1-(4-acetoxybutyl)- and 1-(4-hydroxybutyl)pyrazoles and their tuberculostatic activity. Russ Chem Bull 60, 2396–2400 (2011). https://doi.org/10.1007/s11172-011-0368-4

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  • DOI: https://doi.org/10.1007/s11172-011-0368-4

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