This article is cited in 5 papers

Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane

A. T. Soldatenkov^a, V. V. Shereshovets^a, L. N. Kuleshova^b, V. N. Khrustalev<sup>b

a</sup> Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Potassium permanganate oxidizes a mixture of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (THP) 1 and dicyanomethane to 2-dicyanomethylidenetetrahydropyridine 2, but using manganese dioxide leads to the unusual oxidative hydroxymethylation of 1; subsequent treatment of the 3-hydroxymethyltetrahydropyridine 4 formed with aqueous potassium permanganate results in lactamination, accompanied by aromatization or oxodihydroxylation.

Language: English

DOI: 10.1070/MC1998v008n05ABEH001011

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