Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines

A palladium-mediated multicomponent domino reaction leading to 2-aryl-4-amino-quinolines and 2-aryl-4-amino[1,8]naphthyridines is reported. The scope of the reaction was examined using carbon monoxide, two 2-ethynyl-arylamines, four aryl iodides, and 10 primary amines as substrates. The selection of the appropriate catalytic system was achieved testing several palladium/phosphine systems and overrides previously reported drawbacks associated with the use of primary amines in related reactions. Moreover several features concerning the role of both palladium [(0) and (11)] and phosphines are reported.