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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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