A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls

A 2-pyridone ring is a frequently occurring subunit in natural products, biologically active compounds, and pharmaceutical targets. Thus, the selective synthesis of substituted 2-pyridone derivatives through decoration and/or formation of pyridone rings has been one of the important longstanding sub...

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Published inChemical science (Cambridge) Vol. 9; no. 1; pp. 22 - 32
Main Authors Hirano, Koji, Miura, Masahiro
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.01.2018
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Summary:A 2-pyridone ring is a frequently occurring subunit in natural products, biologically active compounds, and pharmaceutical targets. Thus, the selective synthesis of substituted 2-pyridone derivatives through decoration and/or formation of pyridone rings has been one of the important longstanding subjects in organic synthetic chemistry. This minireview focuses on recent advances in site-selective C-H functionalization on 2-pyridone. The reported procedures are categorized according to the site selectivity that is achieved, and the substrate scope, limitations, mechanism, and controlling factors are briefly summarized. This minireview focuses on recent advances in site-selective C-H functionalization on 2-pyridone which is an important heterocyclic motif in medicinal and pharmaceutical chemistry.
Bibliography:Koji Hirano was born in Aichi, Japan, in 1980. He received his B.S. and Ph.D. degrees from Kyoto University in 2003 and 2008 under the supervision of Professor Koichiro Oshima. He served as a JSPS postdoctoral fellow, working with Professor Tamio Hayashi at Kyoto University from April to September in 2008. He joined the research group of Professor Miura at Osaka University as an assistant professor in October, 2008, and then was promoted to the rank of an associate professor in 2015. His current research interests are organic synthesis and organometallic chemistry, especially the development of new synthetic reactions catalyzed by transition metal catalysts.
Masahiro Miura is a professor of the Graduate School of Engineering, Osaka University. He studied chemistry at Osaka University and received his Ph.D. degree in 1983 under the guidance of Prof. S. Kusabayashi and Prof. M. Nojima. After working in the chemical industry for one and a half years, he started his academic career as an assistant professor at Osaka University. He was promoted to associate professor in 1994 and to full professor in 2005. He also worked as a Humboldt fellow with Prof. K. Griesbaum at Karlsruhe University of Germany from 1990-1991. His current research interests include transition-metal catalysis and the synthesis of functional molecules, especially new π-conjugated aromatic substances.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc04509c