OXIDATIVE REACTIONS OF AZINES. 9. CASCADE AND STAGE OXIDATION OF 1,4-DISUBSTITUTED 1,2,3,6-TETRAHYDROPYRIDINES BY POTASSIUM PERMANGANATE

Abstract

A general scheme was developed for the cascade and stage oxidation of 1,4-disubstituted 1,2,3,6‑tetrahydropyridines by potassium permanganate, based on the successive oxidation of the allylic triad of carbon atoms in the piperideine ring. In the case of 4-aryltetrahydropyridines 2‑oxotetrahydropyridines are formed initially. 3,4-Dihydroxypiperidin-2-ones and finally 1‑aminoalkan-3-ones are then formed. The oxidation of 4-methyl-substituted tetrahydropyridines to the analogous 1-aminoalkanones begins differently – with 3,4-dihydroxylation followed by lactamization of the piperidinediols.

How to Cite
Soldatenkov, A. T.; Temesgen, A. V.; Bekro, I. A. Chem. Heterocycl. Compd. 2001, 37, 1216. [Khim. Geterotsikl. Soedin. 2001, 1332.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1013841325485