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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2299-2306
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7181
Fused [1]Benzazepines. Pentacyclic [1]Benzazepines by Reaction of 1H-[1]Benzazepine-2,5(3H,4H)-dione with Aldehydes

Conrad Kunick*

*Institut für Pharmazie, Universität Hamburg, 20146 Humburg, Germany


Condensation reaction of 1H-[1]benzazepine-2,5(3H,4H)-dione (1) with the aromatic aldehydes (2a-e) in the presence of piperidine furnished 4-benzylidene-1H-[1]benzazepine-2,5(3H,4H)-diones (3a-e), whereas in the presence of potassium hydroxide the 7a,8,15a,15b-tetrahydro-15b-hydroxy-5H-[1]benzazepino[4’,5’:4,5]cyclopenta[1,2-c][1]benzazepine-6,9,15(7H,8aH,14H)-triones (4a-e) were formed. The reaction of 1 with formaldehyde yielded the spiro compound (7) as the product of a Diels-Alder dimerization.