Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles

Chen-Xu Mou; Jin-Wei Yuan; Qian Hu; Bing-Jie Han; Liang-Ru Yang; Yong-Mei Xiao; Lu-Lu Fan; Shou-Ren Zhang; Ling-Bo Qu

doi:10.1039/D2NJ04309B

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Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles†

Chen-Xu Mou,^a Jin-Wei Yuan,

*^a Qian Hu,^a Bing-Jie Han,^a Liang-Ru Yang,

*^a Yong-Mei Xiao,^a Lu-Lu Fan,

^a Shou-Ren Zhang

*^b and Ling-Bo Qu^c

Author affiliations

* Corresponding authors

^a School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China
E-mail: yuanjinweigs@126.com

^b Henan Key Laboratory of Nanocomposites and Applications, Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, P. R. China
E-mail: shourenzhang@infm.hhstu.edu.cn

^c College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China

Abstract

A convenient and efficient copper-catalyzed oxidative arylation of quinoxalin-2(1H)-ones with 3-aminoindazoles is developed for the synthesis of cyanoarylated quinoxalin-2(1H)-ones. Notably, 3-aminoindazoles are employed as efficient arylating agents via the cleavage of two C–N bonds. This oxidative arylation of quinoxalin-2(1H)-ones involves a radical process and undergoes a sequence of 3-aminoindazole oxidation, two C–N bond cleavage, and cyanoaryl radical addition.

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Article information

DOI: https://doi.org/10.1039/D2NJ04309B
Article type: Paper
Submitted: 29 Aug 2022
Accepted: 09 Jan 2023
First published: 10 Jan 2023

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New J. Chem., 2023,47, 3783-3792

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Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles

C. Mou, J. Yuan, Q. Hu, B. Han, L. Yang, Y. Xiao, L. Fan, S. Zhang and L. Qu, New J. Chem., 2023, 47, 3783 DOI: 10.1039/D2NJ04309B

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New Journal of Chemistry

Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles†

Abstract

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Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles

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