Expedient and Diastereoselective Synthesis of Substituted 6,6a-Dihydroisoindolo[2,1-a]quinolin-11(5H)-ones

Abstract

Further synthetic utility of 3-substituted N-arylisoindolinones obtained from N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid mediated anhydrous conditions is reported. Herein, substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones were synthesized from 3-substituted isoindolinones following a NaBH 4 ketone reduction and carbocation-mediated intramolecular electrophilic aromatic substitution using BF 3 •OEt 2. Representative final products were unambiguously characterized by single-crystal X-ray crystallography.