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Oxidative Reactions of Azines. 9. Cascade and Stage Oxidation of 1,4-Disubstituted 1,2,3,6-Tetrahydropyridines by Potassium Permanganate

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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  1. Russian Peoples Friendship University, Moscow, 117193

    A. T. Soldatenkov, A. V. Temesgen & I. A. Bekro

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  1. A. T. Soldatenkov
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  2. A. V. Temesgen
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  3. I. A. Bekro
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Soldatenkov, A.T., Temesgen, A.V. & Bekro, I.A. Oxidative Reactions of Azines. 9. Cascade and Stage Oxidation of 1,4-Disubstituted 1,2,3,6-Tetrahydropyridines by Potassium Permanganate. Chemistry of Heterocyclic Compounds 37, 1216–1222 (2001). https://doi.org/10.1023/A:1013841325485

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