Synthesis of 5a,11b-propanonaphtho[1,2-e][1,2]oxazepines as potential opioid analgesics

Abstract

5a, 11b-Propanonaphtho[1,2-e][1,2]oxazepines have been prepared from dihydro-7,14-cyclocodeinone by the following reaction path: nucleophilic cyclopropane-ring opening, N-oxide formation, Cope reaction and intramolecular O-alkylation. The skeleton of the resulting compounds which have potential as analgesics, is closely similar to that of the parent morphinan, although there is a novel annulation of the nitrogen-containing ring which is further expanded to an oxazepine.