Modular synthesis of non-conjugated N-(quinolin-8-yl) alkenyl amides via cross-metathesis

We report a direct and modular method to access non-conjugated alkenyl amides containing the 8-aminoquinoline (AQ) directing auxiliary and related groups via cross-metathesis. In this way, readily available, AQ-containing, terminal beta, gamma-unsaturated amides can be coupled with various terminal alkenes to furnish internal alkene products that are otherwise difficult to prepare. The value of this family of products stems from their ability to participate in a number of directed alkene functionalization reactions. (C) 2021 Published by Elsevier Ltd.

Automated summary

A direct and modular method has been reported to access non-conjugated alkenyl amides containing the directing auxiliary 8-aminoquinoline (AQ) and related groups via cross-metathesis. This method allows the synthesis of internal alkene products that are difficult to prepare, which can participate in various directed alkene functionalization reactions.