N1-取代基控制的喹喔啉-2(1)-酮与炔烃的铜催化发散式C-H官能化反应用于合成()-烯胺酮和呋喃并[2,3-]喹喔啉

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

作者信息

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

机构信息

Guangxi Key Laboratory of Electrochemical and Magnetochemical Function Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China.

出版信息

Org Lett. 2022 Mar 11;24(9):1859-1864. doi: 10.1021/acs.orglett.2c00454. Epub 2022 Feb 28.

DOI:10.1021/acs.orglett.2c00454

PMID:35225627

Abstract

With control by N1-substituents, the switchable divergent C-H functionalization reaction of quinoxalin-2(1)-ones is achieved for the synthesis of ()-enaminones and furo[2,3-]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.

摘要

通过 N1-取代基的控制，使用铜催化剂和氧化剂的组合实现了喹喔啉-2(1)-酮的可切换发散 C-H 官能化反应，用于合成()-烯胺酮和呋喃并[2,3-]喹喔啉。该新方法具有反应条件温和、原料易得和底物范围广的特点。还进行了克级规模和机理研究。此外，通过 MTT 法测试，所期望的产物对 A549、HepG-2、MCF-7 和 HeLa 细胞表现出优异的抗肿瘤活性。