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Controllable Synthesis of Benzo[b]furo[2,3-d]azepines or Furo[3,2-b]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C–H Amination Reactions

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2025, 90, 1, 357-373
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    Controllable Synthesis of Benzo[b]furo[2,3-d]azepines or Furo[3,2-b]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C–H Amination Reactions
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    • Rong Ma
      Rong Ma
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      More by Rong Ma
    • Yujie Qu
      Yujie Qu
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      More by Yujie Qu
    • Pengcheng Guan
      Pengcheng Guan
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      More by Pengcheng Guan
    • Minghui Liu
      Minghui Liu
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      More by Minghui Liu
    • Yu Han*
      Yu Han
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      *Email: [email protected]
      More by Yu Han
    • Feng Feng*
      Feng Feng
      Faculty of medicine, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      *Email: [email protected]
      More by Feng Feng
    • Chengyu Wang*
      Chengyu Wang
      School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People’s Republic of China
      *Email: [email protected]
      More by Chengyu Wang
      Orcidhttps://orcid.org/0000-0002-9189-1069
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 1, 357–373
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    https://doi.org/10.1021/acs.joc.4c02293
    Published December 12, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    Two novel Pd-catalyzed protocols for the controllable synthesis of benzo[b]furo[2,3-d]azepines and furo[3,2-b]indoles have been developed by intermolecular oxidative annulation of 2-(furan-2-yl)anilines and propargyl carbonates versus intramolecular C–H amination reactions. These two protocols feature great scalability, functional group tolerance, and relatively mild reaction conditions. Notably, the robust methodologies could also provide valuable opportunities for assembling azepine-fused benzothiophene, indole-fused benzothiophene, and indole-fused benzimidazole, which may have potential applications in the synthesis of related pharmaceuticals or polymeric materials.

    Copyright © 2024 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02293.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 1, 357–373
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02293
    Published December 12, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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