Lewis acid-mediated modular route to the synthesis of 3-substituted quinolines from 2-aminobenzyl alcohols and enamine(one)s

Abstract

A Lewis acid-mediated synthesis of 3-substituted quinolines from readily available 2-aminobenzyl alcohols and N,N′-dimethylenamine(one)s is reported. The Friedlander-type reaction described herein is modular and allows the installation of a variety of electron-withdrawing groups (COPh, CN, CO₂Me, NO₂, SO₂Ph) at the 3-position of the quinoline nucleus to afford the final products in moderate to good yields. The reaction proceeds via transamination followed by the formation of a C–C bond by the involvement of a boron complex and aerobic oxidation to offer the product.