Catalyst-Controlled Regioselective Approach to 1-Aminoisoquinolines and/or 1-Aminoisoindolines through Aminative Domino Cyclization of 2-Alkynylbenzonitriles

摘要

A metal-catalyzed regioselective approach towards the synthesis of 1-aminoisoquinolines and/or 1-aminoisindolines through aminative domino cyclization of 2-alkynylbenzonitriles with secondary amines has been developed under solvent-free conditions. It was found that the regioselectivity of the reaction was greatly influenced by the choice of the metal catalyst. Copper-based catalysts favored 6-endo-dig cyclization leading to 1-aminoisoquinolines, whereas other catalysts such as triflates of Zn, Ag, Bi, Sc and Yb favored the formation of 1-aminoisoindolines through 5-exo-dig cyclization.