Base‐Catalyzed Cascade Reaction of ortho‐(Propargylamino)aryl Ketones with N‐, O‐, or S‐Based Nucleophiles for the Synthesis of 3‐Functionalized Quinoline Scaffolds

Abstract

A metal-free and base-catalyzed cascade reaction of ortho-(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N-heterocycles, and thiols through 1,4benzoxazepine intermediates was developed, providing a series of synthetically and medically valuable 3-functionalized quinoline derivatives. The reaction process was easily manipulable and environmentally benign, producing 1.0 equiv. of water as the sole byproduct. Furthermore, bimolecular reactions for the synthesis of products containing two quinoline units were also succesful by utilizing this newly developed protocol.