Synthesis of New 8-Arylisoquinoline Derivatives by Application of Palladium-Catalyzed Suzuki Cross-Coupling Reactions.

2005

Abstract New 8-(het)aryltetrahydroisoquinolines ( 10–14 ), 8-aryltetrahydroisoquinolin-4-ols ( 15 , 16 ), and 8-phenylisoquinolin-4-ol ( 17 ), flexible analogues of aporphine, were synthesized in good yields using palladium-catalyzed Suzuki cross-coupling reactions from 8-bromotetrahydroisoquinolin-4-one ( 6 ) as a common intermediate. We also describe the synthesis of this novel intermediate through an easy and efficient method, which involved intramolecular Friedel–Crafts cyclization.