IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-31063-3.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-31063-3
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-022-31063-3?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    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. 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.
    3. 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.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Anupam Prasoon & Xiaoqing Yu & Mike Hambsch & David Bodesheim & Kejun Liu & Angelica Zacarias & Nguyen Ngan Nguyen & Takakazu Seki & Aerzoo Dianat & Alexander Croy & Gianaurelio Cuniberti & Philippe F, 2023. "Site-selective chemical reactions by on-water surface sequential assembly," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Qingyang Zhao & Le Yu & Yao-Du Zhang & Yong-Qiang Guo & Ming Chen & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "C(alkyl)–C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    3. Lei Zhang & Chen Yang & Chenxi Lu & Xingxing Li & Yilin Guo & Jianning Zhang & Jinglong Lin & Zhizhou Li & Chuancheng Jia & Jinlong Yang & K. N. Houk & Fanyang Mo & Xuefeng Guo, 2022. "Precise electrical gating of the single-molecule Mizoroki-Heck reaction," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31063-3. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.