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Communication | Regular issue | Vol 16, No. 10, 1981, pp.1665-1668
Published online, 1st January, 1970
DOI: 10.3987/R-1981-10-1665
Base-Promoted Isomerization of 4-(Pyrrolylmethyl)-1,2,3,6-tetrahydropyridines

Joan Bosch,* David Mauleón, and Ricardo Granados

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain


The base-promoted isomerization followed by acetic acid treatment of two 4-(pyrrolylmethyl)-1,2,3,6-tetrahydropyridines is studied. 1-Methyl-4-(1-pyrrolylmethyl)-1,2,3,6-tetrahydropyridine (3) gave a mixture of the methanopyrrolodiazocine 1 and pyrrole, the latter arising from a fragmentation reaction. 1-Methyl-4-(1-methyl-2-pyrrolylmethyl)-1,2,3,6-tetrahydropyridine (4) afforded a mixture of recovered tetrahydropyridine and a 4-methylenepiperidine 5 instead of the cyclization product 2.