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Oxidative reactions of azines

5. Ketodihydroxylation and coupling of 4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines with acetone. Molecular and crystal structure of 3,4-dihydroxy-4-(γ-pyridyl)-1-ethylpiperidin-2-one

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Oxidative coupling of 1-alkyl(benzyl)-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4-(γ-pyridyl)piperidin-2-ones. The molecular and crystal structures of one of these products (R=Et) was studied by X-ray diffraction analysis.

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References

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Authors and Affiliations

  1. Russian Peoples' Friendship University, 6 ul. Mikluho-Maklaya, 117198, Moscow, Russian Federation

    A. T. Soldatenkov, I. A. Bekro, S. A. Soldatova, E. Glover, A. Temesgen, L. N. Kuleshova & N. D. Sergeeva

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    V. N. Khrustalev

Authors
  1. A. T. Soldatenkov
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  2. I. A. Bekro
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  3. S. A. Soldatova
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  4. E. Glover
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  5. A. Temesgen
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  6. L. N. Kuleshova
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  7. V. N. Khrustalev
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  8. N. D. Sergeeva
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Additional information

For part 4, see Ref. 1

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2020–2023, November, 1997.

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Soldatenkov, A.T., Bekro, I.A., Soldatova, S.A. et al. Oxidative reactions of azines. Russ Chem Bull 46, 1916–1919 (1997). https://doi.org/10.1007/BF02503786

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  • DOI: https://doi.org/10.1007/BF02503786

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