Search

It has been established that oxidation of a mixture of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and dicyanomethane or formaldehyde with manganese dioxide gives 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, the structure of which was confirmed by X-ray structural analysis. Some oxidative conversions by potassium permanganate of the product formed and its esters have been studied. These included lactamization, aromatization, and oxodihydroxylation.

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.

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.