STUDIES ON THE CHEMISTRY OF ISOINDOLES AN D ISOINDOLENINES .40. 1-METHOXY-2-METHYL-3-ARYL-2H-ISOINDOLES - GENERATION CHARACTERIZATION ISOLATION

1-Methoxy-2-methyl-3-aryl-2H-isoindoles are accessible via an efficien t and economical manner starting from 3-aryl-isoindoline-1-ones; the f our step synthesis makes use of the ambivalent reactivity of the cycli c carbonamide group. The regiospecific O-methylation and NH-deprotonat ion is consecuted by the regiospecific N-methylation of the 3-methoxy- 1-aryl-1H-isoindoles and the chemoselective CH-deprotonation.The elect ronic stabilization of these o-quinonoid hetarenes by an aryl group in 3-position is essential for isolation.