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Updated: Sep 18, 2025

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Copper-Catalyzed Chan-Lam Reaction and Sequential Oxidative Fischer Indole Synthesis to Prepare Indole Derivatives
Jia-Yi Gao1, Xian-Jun Wei1, Si-Yu Chen1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Abstract:
A variety of α-quinazolin-4-yloxy ketones were prepared in moderate to excellent yields through a copper-catalyzed Chan-Lam reaction/[3,3]-rearrangement of N3-hydroxyquinazolinones and alkenyl boronic acids. More importantly, α-quinazolin-4-yloxy ketones could serve as indole precursors through the Fischer indole synthesis procedure by reacting with arylhydrazines in air, which involved nucleophilic substitution, oxidation, and [3,3]-rearrangement in a one-pot. The present cascade reaction highlights a broad substrate scope, good functional group compatibility, and high rearrangement selectivity, and the obtained α-quinazolin-4-yloxy ketones served as high site-marked indole precursors.
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