European Journal of Organic Chemistry issue:25 pages:4861-4867
An efficient diversity-oriented procedure for the two-step synthesis of 3-benzazepines is described. The Cu-I-catalyzed three-component coupling of an aldehyde, an alkyne and an amine (A(3)-coupling) provides the required propargylamines and assures the generation of diversity. The Pd-catalyzed intramolecular acetylene hydroarylation reaction selectively creates the seven-membered 3-benzazepine framework with full control over the ring size and the geometry around the double bond. Microwave irradiation is demonstrated to be highly efficient in promoting both steps.