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...
Saved in:
| Published in | Chemical science (Cambridge) Vol. 9; no. 1; pp. 22 - 32 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
07.01.2018
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | 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. |
|---|---|
| AbstractList | 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. 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. 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. 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.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. |
| Author | Miura, Masahiro Hirano, Koji |
| AuthorAffiliation | Graduate School of Engineering Osaka University Department of Applied Chemistry |
| AuthorAffiliation_xml | – sequence: 0 name: Graduate School of Engineering – sequence: 0 name: Department of Applied Chemistry – sequence: 0 name: Osaka University – name: a Department of Applied Chemistry , Graduate School of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan . Email: k_hirano@chem.eng.osaka-u.ac.jp ; Email: miura@chem.eng.osaka-u.ac.jp |
| Author_xml | – sequence: 1 givenname: Koji surname: Hirano fullname: Hirano, Koji – sequence: 2 givenname: Masahiro surname: Miura fullname: Miura, Masahiro |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29629070$$D View this record in MEDLINE/PubMed |
| BookMark | eNptks9rFDEUx4NUbK29eFcCXkQ6ml8zyXgQyqBWKHhQzyGTeVlTssmazBTqwb_dbLddtRhC8kI-75svee8xOogpAkJPKXlNCe_fWFksES3p7QN0xIigTdfy_mAfM3KITkq5JHVwTlsmH6FD1nesJ5IcoV9nOEApKWKXMi5-hqZAADv7K8BDc47dEushRRP8T7MNcJ2s2VxnP1Un5S3OZvLWhFOc8srEtIbZhODtKZ583grFFV7ltGywiRMuM2RvsU1xzimUJ-ihM6HAye1-jL59eP91OG8uPn_8NJxdNFb0Ym5EO42jA0XkqGw3tlNnjJKWcKDEQUeElb2DFninlHC0U0ZRJhSfOjd1rQB-jN7tdDfLuIbJQn3eBL3Jfm3ytU7G639vov-uV-lKt0q2RKkq8PJWIKcfC5RZr32xEIKJkJaiGWFcUC6krOiLe-hlWnL9wC1Fierr2lfq-d-O9lbuSlMBsgNsTqVkcNr6-aYC1aAPmhK9bQA9yC_DTQMMNeXVvZQ71f_Cz3ZwLnbP_ekm_htvtrvZ |
| CitedBy_id | crossref_primary_10_1002_ijch_202300103 crossref_primary_10_1039_D4RA06210H crossref_primary_10_1021_acs_organomet_8b00185 crossref_primary_10_1039_D0OB02350G crossref_primary_10_1039_D1OB01829A crossref_primary_10_1039_C9CC03893K crossref_primary_10_1039_D4NJ01989J crossref_primary_10_1002_chem_202000672 crossref_primary_10_1002_chem_202101769 crossref_primary_10_1039_D0QO00279H crossref_primary_10_1039_D4CC05324A crossref_primary_10_1002_ajoc_201900190 crossref_primary_10_1002_cssc_201901951 crossref_primary_10_1039_D4CC01904K crossref_primary_10_1002_anie_201812486 crossref_primary_10_1007_s41061_020_00316_4 crossref_primary_10_1039_D3QO02133E crossref_primary_10_1039_D0CC06834A crossref_primary_10_1016_j_tetlet_2020_152017 crossref_primary_10_1021_acscatal_0c00499 crossref_primary_10_1021_acs_orglett_1c00050 crossref_primary_10_1002_cjoc_202100278 crossref_primary_10_1021_acs_orglett_3c02004 crossref_primary_10_1093_bulcsj_bcsj_20230225 crossref_primary_10_1002_chem_202100031 crossref_primary_10_1038_s41467_021_23058_3 crossref_primary_10_1021_acs_orglett_3c01710 crossref_primary_10_1002_anie_202117006 crossref_primary_10_1246_cl_220194 crossref_primary_10_1002_ejoc_201800299 crossref_primary_10_1021_acs_orglett_3c03849 crossref_primary_10_1002_ejoc_202200007 crossref_primary_10_1021_acscatal_1c00750 crossref_primary_10_1039_C9OB02456E crossref_primary_10_1021_acs_orglett_1c01368 crossref_primary_10_1021_acs_orglett_5c00546 crossref_primary_10_1002_asia_201900865 crossref_primary_10_1021_acscatal_0c04205 crossref_primary_10_1021_acs_joc_1c01220 crossref_primary_10_1002_cctc_202002016 crossref_primary_10_1021_acs_orglett_4c00681 crossref_primary_10_1002_adsc_201901582 crossref_primary_10_1002_ajoc_202100584 crossref_primary_10_3390_molecules25030505 crossref_primary_10_1039_D4OB00902A crossref_primary_10_1039_D3QO00018D crossref_primary_10_1039_C8SC05063E crossref_primary_10_1002_ejoc_202100324 crossref_primary_10_1039_D0OB01716G crossref_primary_10_1002_ajoc_202200097 crossref_primary_10_1039_D3OB01354E crossref_primary_10_1039_C8CC02821D crossref_primary_10_1021_acs_orglett_2c00151 crossref_primary_10_1002_ejoc_202300986 crossref_primary_10_1002_anie_201905924 crossref_primary_10_3390_molecules25030673 crossref_primary_10_1039_D2NJ01065H crossref_primary_10_1055_s_0043_1775454 crossref_primary_10_1002_slct_202404352 crossref_primary_10_1016_j_trechm_2019_03_013 crossref_primary_10_1039_C9CC07482A crossref_primary_10_1039_D4SC00316K crossref_primary_10_1002_ejoc_202100336 crossref_primary_10_1021_acs_orglett_0c01277 crossref_primary_10_1039_D2CC05676C crossref_primary_10_1002_anie_201900495 crossref_primary_10_1021_acs_orglett_5c00487 crossref_primary_10_1002_adsc_202101489 crossref_primary_10_1021_acs_orglett_4c04228 crossref_primary_10_1021_acs_orglett_4c04348 crossref_primary_10_1016_j_jscs_2021_101259 crossref_primary_10_1021_acs_joc_1c01566 crossref_primary_10_1021_acscatal_4c00690 crossref_primary_10_34133_2020_9075697 crossref_primary_10_1021_acs_organomet_9b00119 crossref_primary_10_1021_acs_joc_8b02783 crossref_primary_10_1039_C8OB02272K crossref_primary_10_1002_ange_202117006 crossref_primary_10_1039_D2OB00968D crossref_primary_10_1021_jacs_8b01181 crossref_primary_10_1002_ange_201900495 crossref_primary_10_1039_C9SC03672E crossref_primary_10_1021_acscatal_4c07173 crossref_primary_10_1021_acs_joc_4c00449 crossref_primary_10_1002_jhet_3613 crossref_primary_10_3390_molecules29184418 crossref_primary_10_1002_asia_202300144 crossref_primary_10_1002_anie_202006164 crossref_primary_10_1055_a_1981_3213 crossref_primary_10_1039_D4OB01686F crossref_primary_10_1016_j_ccr_2022_214922 crossref_primary_10_1021_acs_joc_3c02819 crossref_primary_10_1055_a_2227_1020 crossref_primary_10_1021_acs_joc_4c00216 crossref_primary_10_1002_asia_202401870 crossref_primary_10_1002_ange_201905924 crossref_primary_10_1002_adsc_202100056 crossref_primary_10_1002_ange_201812486 crossref_primary_10_1002_chem_202001318 crossref_primary_10_1021_acs_orglett_9b03119 crossref_primary_10_1039_D2CC00257D crossref_primary_10_1021_acs_orglett_3c00497 crossref_primary_10_1002_ange_202006164 crossref_primary_10_1055_s_0041_1737326 crossref_primary_10_1016_j_tetlet_2025_155465 crossref_primary_10_1055_a_2017_4176 crossref_primary_10_1039_C8OB00860D crossref_primary_10_1039_D0OB02376K crossref_primary_10_1021_acscatal_8b04553 crossref_primary_10_1002_asia_202000506 crossref_primary_10_1021_acs_orglett_2c03187 crossref_primary_10_1016_j_tet_2019_05_013 crossref_primary_10_1021_acs_orglett_9b02054 crossref_primary_10_1055_s_0043_1773515 crossref_primary_10_1021_acs_orglett_8b02112 crossref_primary_10_3987_COM_19_S_F_16 crossref_primary_10_1002_ajoc_202100258 crossref_primary_10_1039_C9RA10749E crossref_primary_10_1007_s11164_020_04261_1 crossref_primary_10_1055_s_0043_1773490 crossref_primary_10_1039_D3OB00828B crossref_primary_10_1016_j_tet_2024_134206 crossref_primary_10_1039_C8QO00795K crossref_primary_10_1039_C8RA05709E crossref_primary_10_1039_C9OB01061K crossref_primary_10_1002_adsc_202100596 crossref_primary_10_1021_acs_orglett_2c02021 crossref_primary_10_2174_1570193X19666220519090636 crossref_primary_10_1021_acs_joc_4c01169 crossref_primary_10_1021_acscatal_8b02495 crossref_primary_10_1002_chem_202101074 crossref_primary_10_1002_tcr_202000145 crossref_primary_10_1039_D1CC07040A crossref_primary_10_1002_cctc_202301226 crossref_primary_10_1039_D1OB01856F |
| Cites_doi | 10.1002/anie.201200922 10.1021/acs.joc.7b01932 10.1002/9783527627325.ch13 10.1021/ar000209h 10.1039/b908581e 10.1021/ol101818k 10.1055/s-1984-30875 10.1021/acs.chemrev.5b00662 10.1002/anie.201406228 10.1246/cl.150354 10.1021/jm301268u 10.1039/C4CC08116A 10.1002/anie.201511567 10.1021/acs.joc.5b02410 10.1021/acs.accounts.6b00268 10.1039/c2sc20869e 10.1039/C6CS00371K 10.1039/C7OB01277B 10.1002/anie.200906755 10.1039/c0cs00156b 10.1021/cr900184e 10.1021/acs.joc.7b00135 10.1039/p19920000067 10.1002/anie.200806273 10.1021/acs.orglett.6b01762 10.1016/j.tetlet.2007.04.146 10.1016/j.jfluchem.2009.09.007 10.1002/chem.201001363 10.1002/anie.201206115 10.1016/S0968-0896(02)00434-0 10.1021/ja907214t 10.1039/C6RA04388G 10.1021/acs.organomet.7b00256 10.1021/jm034162s 10.1002/anie.201202455 10.1021/ja505579f 10.1002/anie.201201666 10.3987/COM-16-13459 10.1246/bcsj.50.3324 10.2174/138527205774610886 10.1021/cr100379j 10.1002/anie.200902996 10.1039/B306966D 10.1021/acs.joc.5b02349 10.1055/s-0036-1588735 10.1038/nchem.687 10.1002/chem.201301350 10.1021/acs.joc.7b00682 10.1021/acs.orglett.7b02690 10.1021/ja0428309 10.1021/jo4027885 10.1136/thoraxjnl-2012-203035 10.1021/acs.joc.7b01742 10.1039/c0cc00778a 10.1002/anie.201101597 10.1002/cbdv.200490173 10.1021/ja309172t 10.1021/cr900206p 10.1055/s-0029-1219234 10.1021/acs.chemrev.6b00567 10.1039/C5RA20954D 10.1021/acs.orglett.6b02755 10.1016/S0040-4039(01)90707-5 10.1021/ar9000058 10.1021/ol300625u 10.1021/cr950026m 10.1021/acs.orglett.7b01282 10.1055/s-2008-1067256 10.1021/acs.chemrev.5b00514 10.1002/anie.201600791 10.1002/anie.201409669 10.1016/j.bmc.2004.01.016 10.1039/C4CC02166E 10.1021/cr500410y 10.1039/B913880N 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-# 10.1021/cr300503r 10.1021/jo502362k 10.1002/chem.201603263 10.1021/acs.orglett.6b00177 |
| ContentType | Journal Article |
| Copyright | Copyright Royal Society of Chemistry 2018 This journal is © The Royal Society of Chemistry 2018 2018 |
| Copyright_xml | – notice: Copyright Royal Society of Chemistry 2018 – notice: This journal is © The Royal Society of Chemistry 2018 2018 |
| DBID | AAYXX CITATION NPM 7SR 8BQ 8FD JG9 7X8 5PM |
| DOI | 10.1039/c7sc04509c |
| DatabaseName | CrossRef PubMed Engineered Materials Abstracts METADEX Technology Research Database Materials Research Database MEDLINE - Academic PubMed Central (Full Participant titles) |
| DatabaseTitle | CrossRef PubMed Materials Research Database Engineered Materials Abstracts Technology Research Database METADEX MEDLINE - Academic |
| DatabaseTitleList | PubMed CrossRef Materials Research Database MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 2041-6539 |
| EndPage | 32 |
| ExternalDocumentID | PMC5875088 29629070 10_1039_C7SC04509C c7sc04509c |
| Genre | Journal Article Review |
| GroupedDBID | -JG 0-7 0R~ 53G 705 7~J AAEMU AAFWJ AAIWI AAJAE AARTK AAXHV ABEMK ABPDG ABXOH ACGFS ACIWK ADBBV ADMRA AEFDR AENEX AESAV AFLYV AGEGJ AGRSR AGSTE AHGCF AKBGW ALMA_UNASSIGNED_HOLDINGS ANBJS ANUXI AOIJS APEMP AUDPV AZFZN BCNDV BLAPV BSQNT C6K D0L EE0 EF- F5P GROUPED_DOAJ H13 HYE HZ~ H~N O-G O9- OK1 PGMZT R7C R7D RAOCF RCNCU RNS RPM RRC RSCEA RVUXY SKA SKF SKH SKJ SKM SKR SKZ SLC SLF SLH SMJ AAWGC AAYXX ABASK ABIQK ACRPL ADNMO AETIL AFPKN AFRZK AFVBQ AGQPQ AHGXI AKMSF ALSGL ANLMG ASPBG AVWKF CAG CITATION COF ECGLT FEDTE HVGLF J3G J3H J3I L-8 ROL RPMJG NPM 7SR 8BQ 8FD JG9 7X8 5PM |
| ID | FETCH-LOGICAL-c494t-45dbbfe807b8c6b5d6aa87c03e10fe604c79fe5e36884f168a812483d6fd654e3 |
| ISSN | 2041-6520 |
| IngestDate | Thu Aug 21 18:34:16 EDT 2025 Thu Jul 10 22:56:22 EDT 2025 Sun Jul 13 05:14:43 EDT 2025 Thu Apr 03 07:05:27 EDT 2025 Tue Jul 01 03:46:16 EDT 2025 Thu Apr 24 22:50:26 EDT 2025 Tue Dec 17 20:59:18 EST 2024 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 1 |
| Language | English |
| License | This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c494t-45dbbfe807b8c6b5d6aa87c03e10fe604c79fe5e36884f168a812483d6fd654e3 |
| Notes | 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. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ORCID | 0000-0001-9752-1985 0000-0001-8288-6439 |
| OpenAccessLink | http://dx.doi.org/10.1039/c7sc04509c |
| PMID | 29629070 |
| PQID | 2010892019 |
| PQPubID | 2047492 |
| PageCount | 11 |
| ParticipantIDs | crossref_citationtrail_10_1039_C7SC04509C crossref_primary_10_1039_C7SC04509C proquest_journals_2010892019 proquest_miscellaneous_2023413477 rsc_primary_c7sc04509c pubmedcentral_primary_oai_pubmedcentral_nih_gov_5875088 pubmed_primary_29629070 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2018-01-07 |
| PublicationDateYYYYMMDD | 2018-01-07 |
| PublicationDate_xml | – month: 01 year: 2018 text: 2018-01-07 day: 07 |
| PublicationDecade | 2010 |
| PublicationPlace | England |
| PublicationPlace_xml | – name: England – name: Cambridge |
| PublicationTitle | Chemical science (Cambridge) |
| PublicationTitleAlternate | Chem Sci |
| PublicationYear | 2018 |
| Publisher | Royal Society of Chemistry |
| Publisher_xml | – name: Royal Society of Chemistry |
| References | Buck (C7SC04509C-(cit15)/*[position()=1]) 1992 Logan (C7SC04509C-(cit5b)/*[position()=1]) 2012; 14 Miura (C7SC04509C-(cit25)/*[position()=1]) 2016; 18 Studer (C7SC04509C-(cit9a)/*[position()=1]) 2001; vol. 2 Nakao (C7SC04509C-(cit20)/*[position()=1]) 2009; 131 Gulías (C7SC04509C-(cit2r)/*[position()=1]) 2016; 55 Dones (C7SC04509C-(cit23)/*[position()=1]) 2015; 54 Russell (C7SC04509C-(cit8a)/*[position()=1]) 1963; 4 Nakatani (C7SC04509C-(cit4)/*[position()=1]) 2013; 19 Chen (C7SC04509C-(cit18)/*[position()=1]) 2012; 3 Peng (C7SC04509C-(cit36)/*[position()=1]) 2016; 6 Hibi (C7SC04509C-(cit1c)/*[position()=1]) 2012; 55 Hajek (C7SC04509C-(cit1d)/*[position()=1]) 2013; 68 Liu (C7SC04509C-(cit2j)/*[position()=1]) 2011; 111 Yang (C7SC04509C-(cit2t)/*[position()=1]) 2017; 117 Vaillard (C7SC04509C-(cit9b)/*[position()=1]) 2009 Wang (C7SC04509C-(cit5d)/*[position()=1]) 2012; 134 Tobisu (C7SC04509C-(cit5g)/*[position()=1]) 2012; 51 Yoon (C7SC04509C-(cit10a)/*[position()=1]) 2010; 2 Dudnik (C7SC04509C-(cit2g)/*[position()=1]) 2010; 49 Hirano (C7SC04509C-(cit2n)/*[position()=1]) 2015; 44 Najib (C7SC04509C-(cit11)/*[position()=1]) 2016; 92 Chauhan (C7SC04509C-(cit13)/*[position()=1]) 2016; 6 Altenburger (C7SC04509C-(cit35a)/*[position()=1]) 2004; 12 Guo (C7SC04509C-(cit2l)/*[position()=1]) 2015; 115 Jia (C7SC04509C-(cit17)/*[position()=1]) 2001; 34 Kino (C7SC04509C-(cit3)/*[position()=1]) 2010; 131 Guadarrama-Morales (C7SC04509C-(cit7b)/*[position()=1]) 2007; 48 Tang (C7SC04509C-(cit22b)/*[position()=1]) 2017; 36 Studer (C7SC04509C-(cit9c)/*[position()=1]) 2011; 50 Torres (C7SC04509C-(cit1a)/*[position()=1]) 2005; 9 Miura (C7SC04509C-(cit26)/*[position()=1]) 2017; 82 Chotana (C7SC04509C-(cit38b)/*[position()=1]) 2005; 127 Yamaguchi (C7SC04509C-(cit2k)/*[position()=1]) 2012; 51 Anagnostaki (C7SC04509C-(cit14)/*[position()=1]) 2014; 50 Kakiuchi (C7SC04509C-(cit2a)/*[position()=1]) 2008; 2008 Ravelli (C7SC04509C-(cit10d)/*[position()=1]) 2016; 116 Ackermann (C7SC04509C-(cit2d)/*[position()=1]) 2009; 48 Ni (C7SC04509C-(cit34)/*[position()=1]) 2017; 19 Das (C7SC04509C-(cit31)/*[position()=1]) 2017; 82 Bair (C7SC04509C-(cit22a)/*[position()=1]) 2014; 136 Pan (C7SC04509C-(cit35b)/*[position()=1]) 2003; 46 Mkhalid (C7SC04509C-(cit38c)/*[position()=1]) 2010; 110 Yin (C7SC04509C-(cit5c)/*[position()=1]) 2012; 51 Miura (C7SC04509C-(cit39)/*[position()=1]) 2017; 49 Nakatani (C7SC04509C-(cit6)/*[position()=1]) 2014; 79 Daugulis (C7SC04509C-(cit2b)/*[position()=1]) 2009; 42 Ziegler (C7SC04509C-(cit37)/*[position()=1]) 2017; 19 Hartwig (C7SC04509C-(cit38d)/*[position()=1]) 2011; 40 Modak (C7SC04509C-(cit12)/*[position()=1]) 2015; 80 Dickschat (C7SC04509C-(cit5f)/*[position()=1]) 2010; 12 Lagoja (C7SC04509C-(cit1b)/*[position()=1]) 2005; 2 Chen (C7SC04509C-(cit2c)/*[position()=1]) 2009; 48 Li (C7SC04509C-(cit33)/*[position()=1]) 2017; 82 Weintraub (C7SC04509C-(cit35c)/*[position()=1]) 2003; 11 Prier (C7SC04509C-(cit10c)/*[position()=1]) 2013; 113 Yuan (C7SC04509C-(cit2m)/*[position()=1]) 2015; 51 Odani (C7SC04509C-(cit24)/*[position()=1]) 2014; 53 Peng (C7SC04509C-(cit27)/*[position()=1]) 2016; 18 Guchhait (C7SC04509C-(cit5e)/*[position()=1]) 2010 Drapeau (C7SC04509C-(cit2s)/*[position()=1]) 2016; 22 Kumar (C7SC04509C-(cit29)/*[position()=1]) 2017; 15 Wang (C7SC04509C-(cit2p)/*[position()=1]) 2016; 45 Li (C7SC04509C-(cit19)/*[position()=1]) 2016; 81 Narayanam (C7SC04509C-(cit10b)/*[position()=1]) 2011; 40 Osornio (C7SC04509C-(cit7a)/*[position()=1]) 2003 Tamura (C7SC04509C-(cit21)/*[position()=1]) 2012; 51 Biswas (C7SC04509C-(cit28)/*[position()=1]) 2017; 82 Zhu (C7SC04509C-(cit2q)/*[position()=1]) 2016; 55 Koike (C7SC04509C-(cit10e)/*[position()=1]) 2016; 49 Satoh (C7SC04509C-(cit2h)/*[position()=1]) 2010; 16 Suehiro (C7SC04509C-(cit8b)/*[position()=1]) 1977; 50 Das (C7SC04509C-(cit30)/*[position()=1]) 2016; 81 Sun (C7SC04509C-(cit2e)/*[position()=1]) 2010; 46 Lyons (C7SC04509C-(cit2f)/*[position()=1]) 2010; 110 Itahara (C7SC04509C-(cit16)/*[position()=1]) 1984 Li (C7SC04509C-(cit32)/*[position()=1]) 2016; 18 Boyarskiy (C7SC04509C-(cit2o)/*[position()=1]) 2016; 116 Ishiyama (C7SC04509C-(cit38a)/*[position()=1]) 2002; 41 Snider (C7SC04509C-(cit5a)/*[position()=1]) 1996; 96 Ackermann (C7SC04509C-(cit2i)/*[position()=1]) 2010; 46 |
| References_xml | – issn: 2001 issue: vol. 2 end-page: 44 publication-title: Radicals in Organic Synthesis doi: Studer – issn: 2009 end-page: 475 publication-title: in Modern Arylation Methods doi: Vaillard Schulte Studer – volume: 51 start-page: 5679 year: 2012 ident: C7SC04509C-(cit21)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201200922 – volume: 82 start-page: 10989 year: 2017 ident: C7SC04509C-(cit28)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.7b01932 – start-page: 475 volume-title: in Modern Arylation Methods year: 2009 ident: C7SC04509C-(cit9b)/*[position()=1] doi: 10.1002/9783527627325.ch13 – volume: 34 start-page: 633 year: 2001 ident: C7SC04509C-(cit17)/*[position()=1] publication-title: Acc. Chem. Res. doi: 10.1021/ar000209h – volume: 46 start-page: 677 year: 2010 ident: C7SC04509C-(cit2e)/*[position()=1] publication-title: Chem. Commun. doi: 10.1039/b908581e – volume: 12 start-page: 3972 year: 2010 ident: C7SC04509C-(cit5f)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/ol101818k – start-page: 488 year: 1984 ident: C7SC04509C-(cit16)/*[position()=1] publication-title: Synthesis doi: 10.1055/s-1984-30875 – volume: 116 start-page: 9850 year: 2016 ident: C7SC04509C-(cit10d)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.5b00662 – volume: 53 start-page: 10784 year: 2014 ident: C7SC04509C-(cit24)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201406228 – volume: 44 start-page: 868 year: 2015 ident: C7SC04509C-(cit2n)/*[position()=1] publication-title: Chem. Lett. doi: 10.1246/cl.150354 – volume: 55 start-page: 10584 year: 2012 ident: C7SC04509C-(cit1c)/*[position()=1] publication-title: J. Med. Chem. doi: 10.1021/jm301268u – volume: 51 start-page: 1394 year: 2015 ident: C7SC04509C-(cit2m)/*[position()=1] publication-title: Chem. Commun. doi: 10.1039/C4CC08116A – volume: 55 start-page: 11000 year: 2016 ident: C7SC04509C-(cit2r)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201511567 – volume: 81 start-page: 715 year: 2016 ident: C7SC04509C-(cit19)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.5b02410 – volume: 49 start-page: 1937 year: 2016 ident: C7SC04509C-(cit10e)/*[position()=1] publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.6b00268 – volume: 3 start-page: 3231 year: 2012 ident: C7SC04509C-(cit18)/*[position()=1] publication-title: Chem. Sci. doi: 10.1039/c2sc20869e – volume: 45 start-page: 6462 year: 2016 ident: C7SC04509C-(cit2p)/*[position()=1] publication-title: Chem. Soc. Rev. doi: 10.1039/C6CS00371K – volume: 15 start-page: 5457 year: 2017 ident: C7SC04509C-(cit29)/*[position()=1] publication-title: Org. Biomol. Chem. doi: 10.1039/C7OB01277B – volume: 49 start-page: 2096 year: 2010 ident: C7SC04509C-(cit2g)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200906755 – volume: 40 start-page: 1992 year: 2011 ident: C7SC04509C-(cit38d)/*[position()=1] publication-title: Chem. Soc. Rev. doi: 10.1039/c0cs00156b – volume: 110 start-page: 1147 year: 2010 ident: C7SC04509C-(cit2f)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr900184e – volume: 82 start-page: 3612 year: 2017 ident: C7SC04509C-(cit31)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.7b00135 – start-page: 67 year: 1992 ident: C7SC04509C-(cit15)/*[position()=1] publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/p19920000067 – volume: 48 start-page: 5094 year: 2009 ident: C7SC04509C-(cit2c)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200806273 – volume: 18 start-page: 3742 year: 2016 ident: C7SC04509C-(cit25)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/acs.orglett.6b01762 – volume: 48 start-page: 4515 year: 2007 ident: C7SC04509C-(cit7b)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2007.04.146 – volume: 131 start-page: 98 year: 2010 ident: C7SC04509C-(cit3)/*[position()=1] publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2009.09.007 – volume: 16 start-page: 11212 year: 2010 ident: C7SC04509C-(cit2h)/*[position()=1] publication-title: Chem.–Eur. J. doi: 10.1002/chem.201001363 – volume: 51 start-page: 11363 year: 2012 ident: C7SC04509C-(cit5g)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201206115 – volume: 11 start-page: 427 year: 2003 ident: C7SC04509C-(cit35c)/*[position()=1] publication-title: Bioorg. Med. Chem. doi: 10.1016/S0968-0896(02)00434-0 – volume: 131 start-page: 15996 year: 2009 ident: C7SC04509C-(cit20)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja907214t – volume: 6 start-page: 57441 year: 2016 ident: C7SC04509C-(cit36)/*[position()=1] publication-title: RSC Adv. doi: 10.1039/C6RA04388G – volume: 36 start-page: 2761 year: 2017 ident: C7SC04509C-(cit22b)/*[position()=1] publication-title: Organometallics doi: 10.1021/acs.organomet.7b00256 – volume: 46 start-page: 5292 year: 2003 ident: C7SC04509C-(cit35b)/*[position()=1] publication-title: J. Med. Chem. doi: 10.1021/jm034162s – volume: 51 start-page: 7786 year: 2012 ident: C7SC04509C-(cit5c)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201202455 – volume: 136 start-page: 13098 year: 2014 ident: C7SC04509C-(cit22a)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja505579f – volume: 51 start-page: 8960 year: 2012 ident: C7SC04509C-(cit2k)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201201666 – volume: 92 start-page: 1187 year: 2016 ident: C7SC04509C-(cit11)/*[position()=1] publication-title: Heterocycles doi: 10.3987/COM-16-13459 – volume: 50 start-page: 3324 year: 1977 ident: C7SC04509C-(cit8b)/*[position()=1] publication-title: Bull. Chem. Soc. Jpn. doi: 10.1246/bcsj.50.3324 – volume: 9 start-page: 1757 year: 2005 ident: C7SC04509C-(cit1a)/*[position()=1] publication-title: Curr. Org. Chem. doi: 10.2174/138527205774610886 – volume: 111 start-page: 1780 year: 2011 ident: C7SC04509C-(cit2j)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr100379j – volume: 48 start-page: 9792 year: 2009 ident: C7SC04509C-(cit2d)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200902996 – start-page: 2316 year: 2003 ident: C7SC04509C-(cit7a)/*[position()=1] publication-title: Chem. Commun. doi: 10.1039/B306966D – volume: 81 start-page: 842 year: 2016 ident: C7SC04509C-(cit30)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.5b02349 – volume: 49 start-page: 4745 year: 2017 ident: C7SC04509C-(cit39)/*[position()=1] publication-title: Synthesis doi: 10.1055/s-0036-1588735 – volume: 2 start-page: 527 year: 2010 ident: C7SC04509C-(cit10a)/*[position()=1] publication-title: Nat. Chem. doi: 10.1038/nchem.687 – volume: 19 start-page: 7691 year: 2013 ident: C7SC04509C-(cit4)/*[position()=1] publication-title: Chem.–Eur. J. doi: 10.1002/chem.201301350 – volume: 82 start-page: 5337 year: 2017 ident: C7SC04509C-(cit26)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.7b00682 – volume: 19 start-page: 5760 year: 2017 ident: C7SC04509C-(cit37)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b02690 – volume: 127 start-page: 10539 year: 2005 ident: C7SC04509C-(cit38b)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0428309 – volume: 79 start-page: 1377 year: 2014 ident: C7SC04509C-(cit6)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/jo4027885 – volume: 68 start-page: 1037 year: 2013 ident: C7SC04509C-(cit1d)/*[position()=1] publication-title: Thorax doi: 10.1136/thoraxjnl-2012-203035 – volume: 82 start-page: 10263 year: 2017 ident: C7SC04509C-(cit33)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/acs.joc.7b01742 – volume: 46 start-page: 4866 year: 2010 ident: C7SC04509C-(cit2i)/*[position()=1] publication-title: Chem. Commun. doi: 10.1039/c0cc00778a – volume: 50 start-page: 5018 year: 2011 ident: C7SC04509C-(cit9c)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201101597 – volume: 2 start-page: 1 year: 2005 ident: C7SC04509C-(cit1b)/*[position()=1] publication-title: Chem. Biodiversity doi: 10.1002/cbdv.200490173 – volume: 134 start-page: 18834 year: 2012 ident: C7SC04509C-(cit5d)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja309172t – volume: 110 start-page: 890 year: 2010 ident: C7SC04509C-(cit38c)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr900206p – start-page: 1166 year: 2010 ident: C7SC04509C-(cit5e)/*[position()=1] publication-title: Synthesis doi: 10.1055/s-0029-1219234 – volume: 117 start-page: 8787 year: 2017 ident: C7SC04509C-(cit2t)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.6b00567 – volume: 6 start-page: 109 year: 2016 ident: C7SC04509C-(cit13)/*[position()=1] publication-title: RSC Adv. doi: 10.1039/C5RA20954D – volume: 18 start-page: 5376 year: 2016 ident: C7SC04509C-(cit27)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/acs.orglett.6b02755 – volume: 4 start-page: 737 year: 1963 ident: C7SC04509C-(cit8a)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)90707-5 – volume: 42 start-page: 1074 year: 2009 ident: C7SC04509C-(cit2b)/*[position()=1] publication-title: Acc. Chem. Res. doi: 10.1021/ar9000058 – volume: 14 start-page: 2940 year: 2012 ident: C7SC04509C-(cit5b)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/ol300625u – volume: vol. 2 start-page: 44 volume-title: Radicals in Organic Synthesis year: 2001 ident: C7SC04509C-(cit9a)/*[position()=1] – volume: 96 start-page: 339 year: 1996 ident: C7SC04509C-(cit5a)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr950026m – volume: 19 start-page: 3159 year: 2017 ident: C7SC04509C-(cit34)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b01282 – volume: 2008 start-page: 3013 year: 2008 ident: C7SC04509C-(cit2a)/*[position()=1] publication-title: Synthesis doi: 10.1055/s-2008-1067256 – volume: 116 start-page: 5894 year: 2016 ident: C7SC04509C-(cit2o)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.5b00514 – volume: 55 start-page: 10578 year: 2016 ident: C7SC04509C-(cit2q)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201600791 – volume: 54 start-page: 633 year: 2015 ident: C7SC04509C-(cit23)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201409669 – volume: 12 start-page: 1713 year: 2004 ident: C7SC04509C-(cit35a)/*[position()=1] publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2004.01.016 – volume: 50 start-page: 6879 year: 2014 ident: C7SC04509C-(cit14)/*[position()=1] publication-title: Chem. Commun. doi: 10.1039/C4CC02166E – volume: 115 start-page: 1622 year: 2015 ident: C7SC04509C-(cit2l)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr500410y – volume: 40 start-page: 102 year: 2011 ident: C7SC04509C-(cit10b)/*[position()=1] publication-title: Chem. Soc. Rev. doi: 10.1039/B913880N – volume: 41 start-page: 3056 year: 2002 ident: C7SC04509C-(cit38a)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-# – volume: 113 start-page: 5322 year: 2013 ident: C7SC04509C-(cit10c)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr300503r – volume: 80 start-page: 296 year: 2015 ident: C7SC04509C-(cit12)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/jo502362k – volume: 22 start-page: 18654 year: 2016 ident: C7SC04509C-(cit2s)/*[position()=1] publication-title: Chem.–Eur. J. doi: 10.1002/chem.201603263 – volume: 18 start-page: 1064 year: 2016 ident: C7SC04509C-(cit32)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/acs.orglett.6b00177 |
| SSID | ssj0000331527 |
| Score | 2.564185 |
| SecondaryResourceType | review_article |
| Snippet | A 2-pyridone ring is a frequently occurring subunit in natural products, biologically active compounds, and pharmaceutical targets. Thus, the selective... This minireview focuses on recent advances in site-selective C–H functionalization on 2-pyridone which is an important heterocyclic motif in medicinal and... |
| SourceID | pubmedcentral proquest pubmed crossref rsc |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 22 |
| SubjectTerms | Chemistry Natural products Substrates |
| Title | A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/29629070 https://www.proquest.com/docview/2010892019 https://www.proquest.com/docview/2023413477 https://pubmed.ncbi.nlm.nih.gov/PMC5875088 |
| Volume | 9 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3Nb9MwFLe67QAXxNegMCYjuKAuLLEd2-FWRZsq2IYELSqnKHEcLai0Uz8OcNqZK_8hfwnPTuKm6oQAqYoqx0osv1_ee36fCL0Mwoz5uUg9qoPCY5pHXprTwCNFHoQp0Yr6Jhv5_IIPRuztOBx3Oj9aUUurZfZafb8xr-R_qApjQFeTJfsPlHUPhQH4D_SFK1AYrn9F435vAoyqjhU0bmBvYdvamGiguAljoIOeEV6Vza_OujQuAuJdfZuXua3VT_u9eWo9NmbLbaen2VcNevmktB3QK8FnrAo2C8R6HEyFhVI1se6LtpbrqhA0SUPGVdwkh7VsD4MSJKW11b6bfSkd7cuVbX7UO08X6WU5n7UtE4G0lgnhsFTZP5rgUxtcUrewW_M44rPA4yGpXDO6PVbVOGqYdLSFxZrhkpboriylW0LBp6amqhILBfqrH6m16Gvc_Rfvk9PR2VkyPBkPd9AegSMH8My9D59G48_OYudTWvcAdqtu6t3S6Hj9-E0NZ-vYsh19uzNvms1YpWZ4F92pTyO4X0HrHuro6X10y-3gA3TdxxXEMEAMb0IMx7-ufw7wFrgw_FrgeoNraB3hTWAdYQcrbGGFAVa4ghVuYPUQjU5PhvHAq5t2eIpFbOmxMM-yQktfZFLxLMx5mkqhfOAFfqG5z5SICh1qyqVkRcBlalRMSXNe5Dxkmu6j3Sms7jHCRGYpESnXgYxYJnnGlJJEBDkBWZGTqIteNRudqLqivWmsMklsZAWNklh8jC1R4i564eZeVXVcbpx10NArqb_zRWLiRWQEV3jhc3cb6GBca-lUz1ZmDjHqIBOiix5V5HWvIREnEUjWLhIbhHcTTIX3zTvT8tJWeg-lMAeoLtoHiLj5a6g9-fN6n6Lb6-_yAO0u5yv9DHToZXZobU-HNcR_AyVbzto |
| linkProvider | Royal Society of Chemistry |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+lesson+for+site-selective+C%E2%80%93H+functionalization+on+2-pyridones%3A+radical%2C+organometallic%2C+directing+group+and+steric+controls&rft.jtitle=Chemical+science+%28Cambridge%29&rft.au=Hirano%2C+Koji&rft.au=Miura%2C+Masahiro&rft.date=2018-01-07&rft.pub=Royal+Society+of+Chemistry&rft.issn=2041-6520&rft.eissn=2041-6539&rft.volume=9&rft.issue=1&rft.spage=22&rft.epage=32&rft_id=info:doi/10.1039%2Fc7sc04509c&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2041-6520&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2041-6520&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2041-6520&client=summon |