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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1388–1403 | Cite as

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

  • D. L. ObydennovEmail author
  • B. I. Usachev
  • V. Ya. Sosnovskikh
Article

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.

Keywords

comanic acid indoles phenylhydrazine pyrazoles 4-pyrones Fischer reaction regio-selectivity 

Notes

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".

Supplementary material

10593_2014_1603_MOESM1_ESM.pdf (566 kb)
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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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • D. L. Obydennov
    • 1
    Email author
  • B. I. Usachev
    • 1
  • V. Ya. Sosnovskikh
    • 1
  1. 1.Institute of Natural SciencesUral Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia

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