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.

Guang Yang, Zhicheng Xiong, Hongsheng Nie, Meiqin He, Qiong Feng, Xuan Li, Huabin Huang, Shoucai Wang, Fanghua Ji, Guangbin Jiang

Organic letters 2022 Mar 11

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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.

Citation

Guang Yang, Zhicheng Xiong, Hongsheng Nie, Meiqin He, Qiong Feng, Xuan Li, Huabin Huang, Shoucai Wang, Fanghua Ji, Guangbin Jiang. 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. Organic letters. 2022 Mar 11;24(9):1859-1864