Pallado-Catalyzed Cascade Synthesis of 2-Alkoxyquinolines from 1,3-Butadiynamides

Abstract

A novel synthesis strategy to access 2-alkoxyquinoline derivatives via a palladium-driven cascade reaction is disclosed. Unlike classic methods based on the alkylation of 2-quinolones with alkyl halides, the present method benefits from the de novo assembly of the quinoline core starting from 1,3-butadiynamides. Palladium-catalyzed reaction cascades with N-(2-iodophenyl)-N-tosyl-1,3-butadiynamides and primary alcohols as external nucleophiles proceed under mild reaction conditions and selectively deliver a variety of differently functionalized 4-alkenyl 2-alkoxyquinolines in a single batch transformation.

Keywords

• 1,3-diynamides
• ynamides
• [4]cumulenimines
• homogeneous catalysis
• heterocycles
• annulation reactions