Diversity-oriented functionalization of 2-pyridones and uracils

Yong Shang, Chenggui Wu, Qianwen Gao, Chang Liu, Lisha Li, Xinping Zhang, Hong-Gang Cheng, Shanshan Liu and Qianghui Zhou ()
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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
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

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-23058-3

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