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

DD Evans, J Weale and DJ Weyell

Australian Journal of Chemistry 26(6) 1333 - 1336
Published: 1973

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).

Full text doi:10.1071/CH9731333

© CSIRO 1973