Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1 H)-ones with Acyloxy Nitroso Compounds

Runye Gao; Fang Wang; Xiao Geng; Chuan-Ying Li; Lei Wang

doi:10.1021/acs.orglett.2c02703

Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1 H)-ones with Acyloxy Nitroso Compounds

Org Lett. 2022 Oct 7;24(39):7118-7122. doi: 10.1021/acs.orglett.2c02703. Epub 2022 Sep 25.

Authors

Runye Gao^{1

2}, Fang Wang¹, Xiao Geng¹, Chuan-Ying Li², Lei Wang^{1

3}

Affiliations

¹ Advanced Research Institute and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, P. R. China.
² Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China.

PMID: 36153761
DOI: 10.1021/acs.orglett.2c02703

Abstract

Herein, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones, with acyloxy nitroso compounds as a source of radicals, is described. Although the C-H functionalization of quinoxalin-2(1H)-ones has been investigated, its difunctionalization, the simultaneous construction of C-C and N-N bonds directly via the radical relay reaction, has rarely been reported. Moreover, the obtained products underwent sequential reactions to access C7-NO₂ of quinoxalin-2(1H)-ones under mild conditions.