Synthesis of Substituted 4-amino-2-benzazepin-3-ones via N-acyliminium ion cyclizations

Abstract

Two versatile syntheses of 1⁻ and 1,2-disubstituted 2-benzazepinones are presented, using N-acyliminium ions as reactive intermediates. The methodology for 1-substitution is based on the synthesis of benzotriazole adducts, which are cyclized upon addition of AlCl₃. The simultaneous introduction of 1- and 2-substitions is realized by an N-acylation of an imine.