Synthesis of the new (cyclopenta[b]pyrrolo[1,2-d])azepino[4,5-b]indole ring system

Article abstract of DOI:10.1016/0040-4039(96)01215-4

The 2-oxo functionalized title compound 1 was synthesised in 7 steps from tryptamine via rearrangement of the bromoiminium ion 13 in alkaline medium to azepinone 14 with concomitant formation of ketone 15. The ratio 14:15 was shown to depend on the nature of the hydroxide counter-ion.