Synthesis of some tricyclic amines–Hexahydro-1H-indenoazepines and a Hexahydro-1H-benzo-quinoline and -isoquinoline

Abstract

2,3,4,4a,5,6-Hexahydro-1H-indeno[7,1-cd]azepine (6), 2,3,3a,4,5,6- hexahydro-1H-benzo[de]quinoline (10), 2,3,3a,4,5,6-hexahydro-1H- benz[de]isoquinoline (12), isolated as their hydrochlorides, and 2,3,4,4a,5,6-hexahydro-1H-indeno[7,1-bc]azepine (8) have been prepared by lithium aluminium hydride reduction of the corresponding lactams which were synthesized from the appropriate tricyclic ketones by Beckmann rearrangement or Schmidt reaction. The base (8) was also synthesized from 1,2,3,4-tetrahydronaphthalene-1,8-dimethanol (15).