TRANSFORMATIONS OF 1-[2-(ADAMANTAN-1-YL)-2-HYDROXYETHYL]-1,2,3,6-TETRAHYDROPYRIDINES BY THE ACTION OF TRIFLUOROMETHANESULFONIC ACID

Abstract

1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.

Autthors: Vera А. Shadrikova*, Evgeny V. Golovin, Victor B. Rybakov, Yuri N. Klimochkin