Diversity-oriented functionalization of 2-pyridones and uracils

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 succes...

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Published inNature communications Vol. 12; no. 1; pp. 2988 - 11
Main Authors Shang, Yong, Wu, Chenggui, Gao, Qianwen, Liu, Chang, Li, Lisha, Zhang, Xinping, Cheng, Hong-Gang, Liu, Shanshan, Zhou, Qianghui
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 20.05.2021
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
639/638/403/605
639/638/403/933
Alkylation
Alkynes
Bromides
Catalysis
CD3 antigen
Chemistry, Pharmaceutical - methods
Deuterium
Drug Discovery - methods
Feasibility Studies
Fenofibrate
Halides
Humanities and Social Sciences
multidisciplinary
Norbornanes - chemistry
Palladium
Palladium - chemistry
Pharmaceutical Preparations - chemistry
Pharmaceutical sciences
Pharmacology
Pharmacophores
Pyridones - chemistry
Reagents
Science
Science (multidisciplinary)
Thymine
Uracil
Uracil - chemistry
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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/DCO 2 Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD 3 -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. Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors show that palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2- pyridones and uracils.
AbstractList 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.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.
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/DCO 2 Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD 3 -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. Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors show that palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2- pyridones and uracils.
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/DCO 2 Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD 3 -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.
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.Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors show that palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2- pyridones and uracils.
Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors show that palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2- pyridones and uracils.
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/DCO Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD -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.
ArticleNumber 2988
Author Cheng, Hong-Gang
Wu, Chenggui
Li, Lisha
Shang, Yong
Liu, Shanshan
Zhou, Qianghui
Zhang, Xinping
Gao, Qianwen
Liu, Chang
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  organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, and The Institute for Advanced Studies
BackLink https://www.ncbi.nlm.nih.gov/pubmed/34016986$$D View this record in MEDLINE/PubMed
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SSID ssj0000391844
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Snippet Heterocycles 2-pyridone and uracil are privileged pharmacophores. Diversity-oriented synthesis of their derivatives is in urgent need in medicinal chemistry....
Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors...
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SubjectTerms 140/131
140/58
639/638/403/605
639/638/403/933
Alkylation
Alkynes
Bromides
Catalysis
CD3 antigen
Chemistry, Pharmaceutical - methods
Deuterium
Drug Discovery - methods
Feasibility Studies
Fenofibrate
Halides
Humanities and Social Sciences
multidisciplinary
Norbornanes - chemistry
Palladium
Palladium - chemistry
Pharmaceutical Preparations - chemistry
Pharmaceutical sciences
Pharmacology
Pharmacophores
Pyridones - chemistry
Reagents
Science
Science (multidisciplinary)
Thymine
Uracil
Uracil - chemistry
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Title Diversity-oriented functionalization of 2-pyridones and uracils
URI https://link.springer.com/article/10.1038/s41467-021-23058-3
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Volume 12
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