Palladium‐Catalyzed Regioselective Synthesis of 1‐Benzoazepine Carbonitriles from o‐Alkynylanilines via 7‐endo‐dig Annulation and Cyanation

Abstract

AbstractWe herein report a three‐component, one‐pot cascade reaction involving an imination/annulation/cyanation sequence for the synthesis of 1‐benzoazepine carbonitrile derivatives using readily available o‐alkynylanilines, cyclic ketones and trimethylsilyl cyanide. This regio‐ and stereoselective reaction was achieved by combining palladium(II) trifluoroacetate and copper(II) acetate in dimethyl sulfoxide. The important features of this method include a broad substrate scope, the use of trimethylsilyl cyanide as a cyanating agent, the formation of two C−C bonds and one C−N bond, mild reaction conditions and good product yields.magnified image