Studies on 1-Azabicyclo Compounds. XVII. Transannular Reaction of cis- and trans-1, 2, 3, 4, 7, 8, 9, 10-Octahydroazecine and Their Derivatives

Abstract

1-Methyl- and 1-ethyl-cis-octahydroazecine (I and X) were synthesized stereoselectively. Transannular reaction of the trans-N-oxide (VII) leading to decahydro-1-methylazecin-6-one (XI) proceeded more smoothly than that of the cis-N-oxide (VI). However, transannular cyclization between the nitrogen and the double bond of N-acetyl-and N-ethoxycarbonyl-cis-octahydroazecine (VIII and XII) producing 1-azabicyclodecane (XVI) proceeded much more easily than that of the corresponding trans derivatives (IX and XIII).