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Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement

Author

Listed:
  • Qiu Shi

    (South China University of Technology)

  • Zhehui Liao

    (South China University of Technology)

  • Zhili Liu

    (South China University of Technology)

  • Jiajia Wen

    (Chinese Academy of Medical Science)

  • Chenguang Li

    (South China University of Technology)

  • Jiamin He

    (South China University of Technology)

  • Jiazhen Deng

    (South China University of Technology)

  • Shan Cen

    (Chinese Academy of Medical Science)

  • Tongxiang Cao

    (South China University of Technology)

  • Jinming Zhou

    (Zhejiang Normal University)

  • Shifa Zhu

    (South China University of Technology)

Abstract

The dearomative functionalization of aromatic compounds represents a fascinating but challenging transformation, as it typically needs to overcome a great kinetic barrier. Here, a catalyst-free dearomative rearrangement of o-nitrophenyl alkyne is successfully established by leveraging the remote oxygen transposition and a weak N-O bond acceleration. This reaction features high atom-, step- and redox-economy, which provides a divergent entry to a series of biologically important benzazepines and bridged polycycloalkanones. The reaction is proposed to proceed through a tandem oxygen transfer cyclization/(3 + 2) cycloaddition/(homo-)hetero-Claisen rearrangement reaction. The resulting polycyclic system is richly decorated with transformable functionalities, such as carbonyl, imine and diene, which enables diversity-oriented synthesis of alkaloid-like polycyclic framework.

Suggested Citation

  • Qiu Shi & Zhehui Liao & Zhili Liu & Jiajia Wen & Chenguang Li & Jiamin He & Jiazhen Deng & Shan Cen & Tongxiang Cao & Jinming Zhou & Shifa Zhu, 2022. "Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31920-1
    DOI: 10.1038/s41467-022-31920-1
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