Photolysis of Vinylogous Chloroacetamides as a Route to Novel Bridged Heterocycles

Abstract

Photolysis of 1-( chloroacetyl )-8,9-dimethoxy-2,3,5,6-tetrahydropyrrolo[2,1-a] isoquinoline (4a) and 1-( chloroacetyl )-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-benzo[a] quinolizine (4b) in acidified water/ acetonitrile each gave mixtures of two products: 10,11-dimethoxy-1,4,5,6,7,8-hexahydro-3,6-methano-2H-3-benzazecine-7,13-dione (5) plus crude 7,8-dimethoxy-1,2,4,5,9,10-hexahydrobenzo [de] pyrrolo [3,2,1-ij] isoquinoline-9,10-dione (6); and 12-hydroxy-11-methoxy- 1,2,4,5,6,7,8,9-octahydro-3,7-methano-3-benzazacycloundecine-8,14-dione (7) and 8,9-dimethoxy-2,3,5,6,10,11-hexahydro-1H-benzo[de] pyrido [3,2,1ij ]quinoline-10,11-dione (8), respectively. The structures of (5), (7) and (8) were confirmed by X-ray crystallographic studies.