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One-pot synthesis of trifluoromethyl- and nitroso-substituted pyrazolines and pyrazoles and their tuberculostatic activity

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Abstract

3-Trifluoromethyl-substituted 4-nitrosopyrazolines and 4-nitrosopyrazoles were prepared by a one-pot synthesis from trifluoromethyl-containing 1,3-diketones, sodium nitrite in acetic acid, and hydrazines (hydrazine hydrate, methylhydrazine). 3-Trifluoromethylpyrazolines can be converted to pyrazoles on heating. The use of phenylhydrazine in these reactions led to the formation of regioisomeric 4-hydroxyimino-5-(trifluoromethyl)pyrazoline. The structure of heterocycles synthesized was established using X-ray diffraction study, 1H and 19F NMR spectroscopy. The obtained products exhibited considerable 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

    O. G. Khudina, Ya. V. Burgart & V. I. Saloutin

  2. Ural Research Institute of Phthisiopulmonology, 50 ul. XXII Parts’ezda, 620039, Ekaterinburg, Russian Fedetation

    M. A. Kravchenkob

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. Kravchenkob
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Correspondence to V. I. Saloutin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1917–1923, October, 2010.

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Khudina, O.G., Burgart, Y.V., Saloutin, V.I. et al. One-pot synthesis of trifluoromethyl- and nitroso-substituted pyrazolines and pyrazoles and their tuberculostatic activity. Russ Chem Bull 59, 1967–1973 (2010). https://doi.org/10.1007/s11172-010-0341-7

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  • DOI: https://doi.org/10.1007/s11172-010-0341-7

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