Indium-Catalyzed Intramolecular Hydroamidation of Alkynes: An Exo-Dig Cyclization for the Synthesis of Pyranoquinolines through Post-Transformational Reaction

Abstract

An efficient approach for the synthesis of pyranoquinolines through the indium-catalyzed activation of alkynes is reported. Intramolecular hydroamidation of alkynes can proceed through alkyne activation by indium(III) and then 6-exo-dig cyclization, leading to a fused pyran ring with high selectivity, high atom economy, and good to excellent yields. The cyclization was accomplished through the oxygen, not the nitrogen, of the amide functional group.