Abstract:
The preparation of benzazepinoindoles, a fused heterocycles with a benzazepine moiety was realised via an intramolecular 7-endo trig Pictet-Spengler cyclization. The precursors comprising C-3- or C-2-linked o-aminobenzyl indoles (5 and 6) required for the cyclization were obtained by treating either indoles with o-nitrobenzyl bromide followed by reduction of the nitro group or by treating 2-nitrophenylacetic acid with DCC/DMAP followed by reduction of the aryl nitro functionality. The resulting substrates 5 and 6 were then subjected to the 7-endo trig Pictet-Spengler reaction with a variety of aldehydes and ketones to furnish new polycyclic structures benzazepinoindoles.
