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    Skeletal reorganization reactions have emerged as an intriguing tool for converting readily available compounds into complicated molecules inaccessible by traditional methods. Herein, we report a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. In the presence of Rh/acid catalysis, cycloheptatriene can selectively couple with anilines to deliver fused 1,2-dihydroquinoline products. Mechanistic studies indicate that the retro-Mannich type ring-opening and subsequent intramolecular Povarov reaction account for the ring reorganization. Our mechanistic studies also revealed that skeleton-reorganizing amination between anilines and cycloalkenones can be achieved with acid. The synthetic utilization of this skeleton-reorganizing coupling reaction was showcased with a gram-scale reaction, synthetic derivatizations, and the late-stage modification of commercial drugs. © 2022 Wiley-VCH GmbH.


    Ding-Wei Ji, Yan-Cheng Hu, Xiang-Ting Min, Heng Liu, Wei-Song Zhang, Ying Li, Yongjin J Zhou, Qing-An Chen. Skeleton-Reorganizing Coupling Reactions of Cycloheptatriene and Cycloalkenones with Amines. Angewandte Chemie (International ed. in English). 2023 Jan 09;62(2):e202213074

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    PMID: 36372782

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