Issue 8, 2023

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
29 Aug 2022
Accepted
09 Jan 2023
First published
10 Jan 2023

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

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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