OXIDATIVE REACTIONS OF AZINES. 6. LACTAMIZATION OF 4-ARYL- AND 4-PHENETHENYL-SUBSTITUTED 1,2,3,6-TETRAHYDROPYRIDINES AND DIHYDROXYLATION OF 4-ARYL-1,2,5,6-TETRAHYDROPYRID-2-ONES USING POTASSIUM PERMANGANATE

А. Т. Солдатенков, А. В. Темесген, И. А. Бекро, С. А. Солдатова, Н. И. Головцов, Н. Д. Сергеева

Abstract


Oxidation of 4-phenyl-, 4-(4-pyridyl)-, and 4-phenethenyl-1,2,3,6-tetrahydropyridines with potassium permanganate can stop at the stage of the introduction of an oxo group into the allyl C(2) position of the piperideine fragment. In contrast to their precursors, 4-aryltetrahydropyridin-2-ones obtained in this way can be converted to 3,4-dihydroxy-2-oxopiperidines under Wagner reaction conditions.

Authors: A. T. Soldatenkov, A. V. Temesgen, I. A. Bekro, S. A. Soldatova, N. I. Golovtsov, and N. D. Sergeeva.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (12), pp 1426-1430

http://link.springer.com/article/10.1023/A%3A1017570313032


Keywords


tetrahydropyridines; tetrahydropyridin-2-ones; dihydroxylation; lactamization; potassium permanganate oxidation

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