Reactivity of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and their isomerization initiated by acids and bases

Abstract

Study of isomerization of 5-endo-hydroxy-4-azatricyclo[5.2.1.0 2,6 ]dec-8-en-3-ones under the action of Lewis acids (MgBr 2 , AlCl 3 ), CF 3 COOH, and NaH showed that the optimum catalyst of the process was trifluoroacetic acid. In reaction of 4-benzyl-5-endo-hydroxy-4-azatricyclo-[5.2.1.0 2,6 ]dec-8-en-3-one with anhydrous AlCl 3 in benzene was unexpectedly isolated N-benzyl-3-(diphenylmethyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide. A convenient method was developed for the preparation of 5-exo-alkoxy-4-alkyl(aryl)-4azatricyclo[5.2.1.0 2,6 ]dec-8-en-3-ones.