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Studies on the Chemistry of Isoindoles and Isoindolenines, XXXX. 1-Methoxy-2-methyl-3-aryl-2H-isoindoles: Generation - Characterization - Isolation
Clemens, Andrea,Kreher, Richard P.
, p. 1257 - 1269 (2007/10/02)
1-Methoxy-2-methyl-3-aryl-2H-isoindoles are accessible via an efficient and economical manner starting from 3-aryl-isoindoline-1-ones; the four step synthesis makes use of the ambivalent reactivity of the cyclic carbonamide group.The regiospecific O-methylation and NH-deprotanation is consecuted by the regiospecific N-methylation of the 3-methoxy-1-aryl-1H-isoindoles and the chemoselective CH-deprotonation.The electronic stabilization of these o-quinonoid hetarenes by an aryl group in 3-position is essential for isolation.
