Transformations of 1-2-(Adamantan-1-Yl)-2-Hydroxyethyl-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid

摘要

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-azabicyclo3.3.1non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.