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Reactions of 2-Mono- and 2,6-Disubstituted 4-Pyrones with Phenylhydrazine as General Method for the Synthesis of 3-(N-Phenylpyrazolyl)Indoles

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Chemistry of Heterocyclic Compounds Aims and scope

Phenylhydrazine reacted regioselectively with 6-substituted 4-pyrone-2-carboxylic acids (or esters) in protic and aprotic solvents, leading to phenylhydrazones of 3-(3-R-1-phenylpyrazol-5-yl)- or 3-(5-R-1-phenylpyrazol-3-yl)pyruvic acids (or esters), respectively. 6-Di(tri)fluoromethylcomanic acids (or esters) reacted analogously, forming the corresponding phenylhydrazones with RF group in the side chain. The obtained phenylhydrazones underwent Fischer reaction under acidic conditions, forming the respective 3-(N-phenylpyrazolyl)indoles. In contrast to comanic acid and its ester, the reactions of 2-substituted 4-pyrones occurred non-selectively and gave mixtures of regioisomeric pyrazoles with phenylhydrazone group in the side chain or 3-(N-phenylpyrazolyl)indoles. A mechanism was proposed to explain the effect of solvent on the course of reaction.

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This work received financial support from the Russian Foundation for Basic Research (project No. 14-03-31925) and the development program at Ural Federal University for the winners of competition "Young scientists of Ural Federal University".

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Authors and Affiliations

  1. Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    D. L. Obydennov, B. I. Usachev & V. Ya. Sosnovskikh

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  1. D. L. Obydennov
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  2. B. I. Usachev
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  3. V. Ya. Sosnovskikh
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Correspondence to D. L. Obydennov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1510-1527, October, 2014.

Electronic supplementary material

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ESM 1

Supplementary information file, containing synthetic procedures and spectral data for compounds Z- 2c, 3a,c, E- 4d, 5d, E- 10a,b, 11a,b, E- 12a,b, 13a,b, E-15b, E-16b, 17b, 18b is available to authorized users. (PDF 565 kb)

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Obydennov, D.L., Usachev, B.I. & Sosnovskikh, V.Y. Reactions of 2-Mono- and 2,6-Disubstituted 4-Pyrones with Phenylhydrazine as General Method for the Synthesis of 3-(N-Phenylpyrazolyl)Indoles. Chem Heterocycl Comp 50, 1388–1403 (2015). https://doi.org/10.1007/s10593-014-1603-3

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  • DOI: https://doi.org/10.1007/s10593-014-1603-3

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