Studies on the Oxidation of N-Substituted-dibenz [b, f] azepines. II. Syntheses and Reactions of 5H-Dibenz [b, f] azepine 10, 11-Oxides

Abstract

The oxidation of various 5H-N-alkyl-10, 11-substituted-dibenz [b, f] azepines with m-chloroperbenzoic acid (m-CPBA) was examined. The oxidation of 5H-N-benzyl-10-substituted-dibenz [b, f] azepine (V) gave N-benzyl-9-formyl-9-substituted-9H, 10H-acridine (VI), while the oxidation of 5H-N-benzyl-10, 11-disubstituted-dibenz [b, f] azepine (VII) gave the corresponding 10, 11-oxide (VIII). The chemical reactivities with several nucleophiles and the acid-catalyzed reactions of 5H-dibenz [b, f] azepine 10, 11-oxides are also discussed.