Polycondensed Heterocycles. Part 11: Preparation and Regioselective Reductions of 5-Phenyl-4H-pyrrolo[1,2-a][1]benzazepin-4-one

The Wadsworth–Emmons olefination between 2-(1H-pyrrol-1-yl)benzaldehyde and methyl α-(diethylphosphonyl)phenylacetate leads exclusively to the cis-isomer of methyl 2-(1H-pyrrol-1-yl)-α-phenylcinnamate, which, after transformation into the corresponding acid chloride, was easily cyclised to the title enone. This latter was regioselectively reduced to the corresponding saturated ketone or unsaturated alcohol, under different experimental conditions. An improved preparation of starting 2-(1H-pyrrol-1-yl)benzaldehyde is also reported.