American Chemical Society
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Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2‑Aryl-3-(2-aminoaryl)quinoxalines

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journal contribution
posted on 2022-04-14, 19:14 authored by Jianwei Yan, Linxia Zheng, Jiangfei Wang, Xiaomin Liu, Youhong Hu
A mild oxidative sequential tandem reaction was developed to rapidly generate 2-aryl-3-(2-aminoaryl) quinoxalines. This method exploited 2-substituted indoles as substrate to form quinoxalines in a one-pot reaction. The key to this tandem reaction was the formation of 3-iodoindoles, which underwent Kornblum-type oxidation with DMSO to generate active imine 2-substitued 3H-indol-3-ones. The active imines were captured in situ by 1,2-diaminobenzenes to construct diverse quinoxalines. The transformation can be accomplished at room temperature with excellent functional group tolerance.