Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1<i>H</i>)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (<i>Z</i>)-Enaminones and Furo[2,3-<i>b</i>]quinoxalines
Guang Yang, Zhicheng Xiong, Hongsheng Nie, Meiqin He, Qiong Feng, Xuan Li, Huabin Huang, Shoucai Wang, Fanghua Ji, Guangbin Jiang
Abstract
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.
Topics & Concepts
ChemistryCatalysisSurface modificationCopperMedicinal chemistryCombinatorial chemistryDivergent synthesisStereochemistryOrganic chemistryPhysical chemistrySynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms