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

A convenient and efficient copper-catalyzed oxidative arylation of quinoxalin-2(1 H )-ones with 3-aminoindazoles is developed for the synthesis of cyanoarylated quinoxalin-2(1 H )-ones. Notably, 3-aminoindazoles are employed as efficient arylating agents via the cleavage of two C–N bonds. This oxida...

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Bibliographic Details
Published in:New journal of chemistry 2023-02, Vol.47 (8), p.3783-3792
Main Authors: Mou, Chen-Xu, Yuan, Jin-Wei, Hu, Qian, Han, Bing-Jie, Yang, Liang-Ru, Xiao, Yong-Mei, Fan, Lu-Lu, Zhang, Shou-Ren, Qu, Ling-Bo
Format: Article
Language:English
Subjects:
Bonding agents
Cleavage
Copper
Oxidation
Ring opening
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Summary:A convenient and efficient copper-catalyzed oxidative arylation of quinoxalin-2(1 H )-ones with 3-aminoindazoles is developed for the synthesis of cyanoarylated quinoxalin-2(1 H )-ones. Notably, 3-aminoindazoles are employed as efficient arylating agents via the cleavage of two C–N bonds. This oxidative arylation of quinoxalin-2(1 H )-ones involves a radical process and undergoes a sequence of 3-aminoindazole oxidation, two C–N bond cleavage, and cyanoaryl radical addition.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ04309B