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Diversity-oriented functionalization of 2-pyridones and uracils

Author

Listed:
  • Yong Shang

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Chenggui Wu

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies
    Anhui University of Chinese Medicine)

  • Qianwen Gao

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Chang Liu

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Lisha Li

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Xinping Zhang

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Hong-Gang Cheng

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Shanshan Liu

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

  • Qianghui Zhou

    (College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies)

Abstract

Heterocycles 2-pyridone and uracil are privileged pharmacophores. Diversity-oriented synthesis of their derivatives is in urgent need in medicinal chemistry. Herein, we report a palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2-pyridones and uracils. The success of this research depends on the use of two unique norbornene derivatives as the mediator. Readily available alkyl halides/tosylates and aryl bromides are utilized as ortho-alkylating and -arylating reagents, respectively. Widely accessible ipso-terminating reagents, including H/DCO2Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD3-labeled 2-pyridones, bicyclic 2-pyridones, 2-pyridone-fenofibrate conjugate, axially chiral 2-pyridone (97% ee), as well as uracil and thymine derivatives, can be quickly prepared in a predictable manner (79 examples reported), which will be very useful in new drug discovery.

Suggested Citation

  • Yong Shang & Chenggui Wu & Qianwen Gao & Chang Liu & Lisha Li & Xinping Zhang & Hong-Gang Cheng & Shanshan Liu & Qianghui Zhou, 2021. "Diversity-oriented functionalization of 2-pyridones and uracils," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23058-3
    DOI: 10.1038/s41467-021-23058-3
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