Accessing Tetrahydroquinaldic Amide and Homoproline Derivatives by Dearomative Difunctionalization of Heteroaromatics

Abstract

This study reports the first synthesis of tetrahydroquinaldic and tetrahydropicolinic amides using readily available quinolines and pyridines through dearomative difunctionalization and hydrolysis under transition‐metal‐ and reductant‐free conditions. The prepared amide products could be easily oxidized to the corresponding quinaldic and picolinic amides. Furthermore, the chemical reactivity of the amide group has been explored to develop convenient methods for their conversion to other common organic functional groups.