TY - JOUR
T1 - Photolysis of Vinylogous Chloroacetamides as a
AU - Bremner, J.B.
AU - Eschler, B.M.
AU - Skelton, Brian
AU - White, Allan
PY - 1994
Y1 - 1994
N2 - 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[3,2,1-ij]quinoline-10,11-dione (8), respectively. The structures of (5), (7) and (8) were confirmed by X-ray crystallographic studies.
AB - 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[3,2,1-ij]quinoline-10,11-dione (8), respectively. The structures of (5), (7) and (8) were confirmed by X-ray crystallographic studies.
U2 - 10.1071/CH9941935
DO - 10.1071/CH9941935
M3 - Article
SN - 0004-9425
VL - 47
SP - 1935
EP - 1952
JO - Australian Journal of Chemistry: an international journal for chemical science
JF - Australian Journal of Chemistry: an international journal for chemical science
ER -