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Reactions of trifluoro- and hexafluoroacetylacetones with thiobenzoylhydrazine

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Abstract

The reaction of thiobenzoylhydrazine with trifluoroacetylacetone leads to the product of condensation at the CH3C=O bond with the 5-hydroxy-2-pyrazoline structure. The tautomeric transition to the 2,3-dihydro-1,3,4-thiadiazole isomer occurs in solution. This isomer undergoes the cleavage to 2-methyl-5-phenyl-1,3,4-thiadiazole and trifluoroacetone. The reaction of thiobenzoylhydrazine with hexafluoroacetylacetone affords one of diastereomers of [3,5-dihydroxy-3,5-bis(trifluoromethyl)pyrazolidin-1-yl](phenyl)thioketone, which at equilibrium is transformed in solution into the second diastereomer of the 3,5-dihydroxypyrazolidine form followed by the elimination of water elements and formation of a tautomeric 5-hydroxy-2-pyrazoline-2,3-dihydro-1,3,4-thiadiazole mixture.

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Authors and Affiliations

  1. S. M. Kirov Military Medical Academy, 6 ul. Akad. Lebedeva, 194044, Saint Petersburg, Russian Federation

    V. V. Alekseyev

  2. Saint Petersburg State University, 26 Universitetsky prosp., 198504, Saint Petersburg, Russian Federation

    V. V. Pakal’nis, I. V. Zerova & S. I. Yakimovich

Authors
  1. V. V. Alekseyev
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  2. V. V. Pakal’nis
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  3. I. V. Zerova
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  4. S. I. Yakimovich
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Correspondence to V. V. Alekseyev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0855–0859, April, 2012.

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Alekseyev, V.V., Pakal’nis, V.V., Zerova, I.V. et al. Reactions of trifluoro- and hexafluoroacetylacetones with thiobenzoylhydrazine. Russ Chem Bull 61, 858–862 (2012). https://doi.org/10.1007/s11172-012-0120-8

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  • DOI: https://doi.org/10.1007/s11172-012-0120-8

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