Oxidative reactions of azines |
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| Authors: | A. T. Soldatenkov I. A. Bekro S. A. Soldatova E. Glover A. Temesgen L. N. Kuleshova V. N. Khrustalev N. D. Sergeeva |
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| Affiliation: | (1) Russian Peoples' Friendship University, 6 ul. Mikluho-Maklaya, 117198 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
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| 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. For part 4, see Ref. 1 Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2020–2023, November, 1997. |
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| Keywords: | 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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