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Rapid syntheses of N-fused heterocycles via acyl-transfer in heteroaryl ketones

Author

Listed:
  • Dan Ye

    (Northwest University)

  • Hong Lu

    (Northwest University)

  • Yi He

    (Northwest University)

  • Zhaojing Zheng

    (Northwest University)

  • Jinghao Wu

    (Northwest University)

  • Hao Wei

    (Northwest University)

Abstract

The wide-ranging potencies of bioactive N-fused heterocycles inspire the development of synthetic transformations that simplify preparation of their complex, diverse structural motifs. Heteroaryl ketones are ubiquitous, readily available, and inexpensive molecular scaffolds, and are thus synthetically appealing as precursors in preparing N-fused heterocycles via intramolecular acyl-transfer. To best of our knowledge, acyl-transfer of unstrained heteroaryl ketones remains to be demonstrated. Here, we show an acyl transfer-annulation to convert heteroaryl ketones to N-fused heterocycles. Driven via aromatisation, the acyl of a heteroaryl ketone can be transferred from the carbon to the nitrogen of the corresponding heterocycle. The reaction commences with the spiroannulation of a heteroaryl ketone and an alkyl bromide, with the resulting spirocyclic intermediate undergoing aromatisation-driven intramolecular acyl transfer. The reaction conditions are optimised, with the reaction exhibiting a broad substrate scope in terms of the ketone and alkyl bromide. The utility of this protocol is further demonstrated via application to complex natural products and drug derivatives to yield heavily functionalised N-fused heterocycles.

Suggested Citation

  • Dan Ye & Hong Lu & Yi He & Zhaojing Zheng & Jinghao Wu & Hao Wei, 2022. "Rapid syntheses of N-fused heterocycles via acyl-transfer in heteroaryl ketones," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31063-3
    DOI: 10.1038/s41467-022-31063-3
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    References listed on IDEAS

    as
    1. Yan Xu & Xiaotian Qi & Pengfei Zheng & Carlo C. Berti & Peng Liu & Guangbin Dong, 2019. "Deacylative transformations of ketones via aromatization-promoted C–C bond activation," Nature, Nature, vol. 567(7748), pages 373-378, March.
    2. Ying Xia & Gang Lu & Peng Liu & Guangbin Dong, 2016. "Catalytic activation of carbon–carbon bonds in cyclopentanones," Nature, Nature, vol. 539(7630), pages 546-550, November.
    3. Helen M. Burke & Lauren McSweeney & Eoin M. Scanlan, 2017. "Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology," Nature Communications, Nature, vol. 8(1), pages 1-16, August.
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