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Russian Chemical Bulletin

, Volume 46, Issue 11, pp 1916–1919 | Cite as

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
  • A. T. Soldatenkov
  • I. A. Bekro
  • S. A. Soldatova
  • E. Glover
  • A. Temesgen
  • L. N. Kuleshova
  • V. N. Khrustalev
  • N. D. Sergeeva
Organic Chemistry

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.

Key words

oxidative coupling, ketodihydroxylation, 1-R-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines, 1-R-3,4-dihydroxy-4-(γ-pyridyl)piperidin-2-ones, 1-R-2-acetylmethylene-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines NMR, X-ray diffraction analysis molecular and crystal structures 

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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • A. T. Soldatenkov
    • 1
  • I. A. Bekro
    • 1
  • S. A. Soldatova
    • 1
  • E. Glover
    • 1
  • A. Temesgen
    • 1
  • L. N. Kuleshova
    • 1
  • V. N. Khrustalev
    • 2
  • N. D. Sergeeva
    • 1
  1. 1.Russian Peoples' Friendship UniversityMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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