Copper-Catalyzed Divergent C-H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

With control by N1-substituents, the switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones is achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using the combination of a copper catalyst and an oxidant. This new protocol features mild reaction conditions, readily available materials, and a broad substrate scope. Gram-scale and mechanistic studies were also investigated. Furthermore, the desired products exhibited excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells, which were tested by MTT assay.

Automated summary

With control by N1-substituents, switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones was achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using copper catalyst and oxidant. The method features mild reaction conditions, readily available materials, and a broad substrate scope, and the desired products showed excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells.