Study of regioselectivity of intramolecular cyclization of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10- oxatricyclo[5.2.1.01,5]dec-8-enes

Regioselectivity of the intramolecular electrophilic substitution in a series of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy- 4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes in reactions with phosphoric acid was studied. The reactions of N-(m-R-phenyl)-substituted derivatives proceed nonregioselectively to form mixtures of 2-R- and 4-R-substituted isoindolo[2,1-a]quinolines, whereas the reactions of N-(α-naphthyl)-substituted derivatives occur regioselectively at the β position of the naphthyl fragment. © 2004 Springer Science+Business Media, Inc.