Competitive intramolecular C-C vs. C-O bond coupling reactions toward C6 ring-fused 2-pyridone synthesis.
Identifieur interne : 000048 ( PubMed/Checkpoint ); précédent : 000047; suivant : 000049Competitive intramolecular C-C vs. C-O bond coupling reactions toward C6 ring-fused 2-pyridone synthesis.
Auteurs : T. Lepitre [France] ; C. Pintiala ; K. Muru ; S. Comesse ; A. Rebbaa ; A M Lawson ; A. DaïchSource :
- Organic & biomolecular chemistry [ 1477-0539 ] ; 2016.
Abstract
An interesting competitive C-C vs. C-O bond coupling reaction on N,3,5-trisubstituted pyridones is reported. These coupling reactions provided selective access to C- or O-ring-fused pyridones, both at the challenging C6-pyridone position. 1,6-C-Annulated pyridones were generally achieved in good yields with excellent chemoselectivity under Pd(0) conditions. On the other hand, full C6-regioselective Csp(2) aryloxylation was achieved under oxidative coupling promoted by silver salts to access 5,6-O-annulated pyridones. Based on various experiments and observations, mechanistic evidence of these competitive reactions was provided and it was proposed that C-O bond formation proceeded through radical cyclization. These processes were performed under mild reaction conditions and offer an efficient and attractive methodology to selectively access a large scope of C-arylated and O-arylated pyridones of biological interest.
DOI: 10.1039/c6ob00303f
PubMed: 26976735
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Lepitre</name><affiliation wicri:level="3"><nlm:affiliation>Laboratoire de Chimie, URCOM, EA 3221, INC3M CNRS FR-3038, Normandie Université (Université du Havre), UFR des Sciences et Techniques de l'Université du Havre, 25 Rue Philippe Lebon, B.P. 1123, F-76063 Le Havre Cedex, France. lawsona@univ-lehavre.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie, URCOM, EA 3221, INC3M CNRS FR-3038, Normandie Université (Université du Havre), UFR des Sciences et Techniques de l'Université du Havre, 25 Rue Philippe Lebon, B.P. 1123, F-76063 Le Havre Cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="Pintiala, C" sort="Pintiala, C" uniqKey="Pintiala C" first="C" last="Pintiala">C. Pintiala</name></author><author><name sortKey="Muru, K" sort="Muru, K" uniqKey="Muru K" first="K" last="Muru">K. Muru</name></author><author><name sortKey="Comesse, S" sort="Comesse, S" uniqKey="Comesse S" first="S" last="Comesse">S. Comesse</name></author><author><name sortKey="Rebbaa, A" sort="Rebbaa, A" uniqKey="Rebbaa A" first="A" last="Rebbaa">A. Rebbaa</name></author><author><name sortKey="Lawson, A M" sort="Lawson, A M" uniqKey="Lawson A" first="A M" last="Lawson">A M Lawson</name></author><author><name sortKey="Daich, A" sort="Daich, A" uniqKey="Daich A" first="A" last="Daïch">A. Daïch</name></author></analytic><series><title level="j">Organic & biomolecular chemistry</title><idno type="eISSN">1477-0539</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">An interesting competitive C-C vs. C-O bond coupling reaction on N,3,5-trisubstituted pyridones is reported. These coupling reactions provided selective access to C- or O-ring-fused pyridones, both at the challenging C6-pyridone position. 1,6-C-Annulated pyridones were generally achieved in good yields with excellent chemoselectivity under Pd(0) conditions. On the other hand, full C6-regioselective Csp(2) aryloxylation was achieved under oxidative coupling promoted by silver salts to access 5,6-O-annulated pyridones. Based on various experiments and observations, mechanistic evidence of these competitive reactions was provided and it was proposed that C-O bond formation proceeded through radical cyclization. These processes were performed under mild reaction conditions and offer an efficient and attractive methodology to selectively access a large scope of C-arylated and O-arylated pyridones of biological interest.</div></front></TEI><pubmed><MedlineCitation Status="In-Process" Owner="NLM"><PMID Version="1">26976735</PMID><DateCreated><Year>2016</Year><Month>3</Month><Day>30</Day></DateCreated><DateRevised><Year>2016</Year><Month>3</Month><Day>30</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1477-0539</ISSN><JournalIssue CitedMedium="Internet"><Volume>14</Volume><Issue>14</Issue><PubDate><Year>2016</Year><Month>Apr</Month><Day>14</Day></PubDate></JournalIssue><Title>Organic & biomolecular chemistry</Title><ISOAbbreviation>Org. Biomol. Chem.</ISOAbbreviation></Journal><ArticleTitle>Competitive intramolecular C-C vs. C-O bond coupling reactions toward C6 ring-fused 2-pyridone synthesis.</ArticleTitle><Pagination><MedlinePgn>3564-73</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1039/c6ob00303f</ELocationID><Abstract><AbstractText>An interesting competitive C-C vs. C-O bond coupling reaction on N,3,5-trisubstituted pyridones is reported. These coupling reactions provided selective access to C- or O-ring-fused pyridones, both at the challenging C6-pyridone position. 1,6-C-Annulated pyridones were generally achieved in good yields with excellent chemoselectivity under Pd(0) conditions. On the other hand, full C6-regioselective Csp(2) aryloxylation was achieved under oxidative coupling promoted by silver salts to access 5,6-O-annulated pyridones. Based on various experiments and observations, mechanistic evidence of these competitive reactions was provided and it was proposed that C-O bond formation proceeded through radical cyclization. These processes were performed under mild reaction conditions and offer an efficient and attractive methodology to selectively access a large scope of C-arylated and O-arylated pyridones of biological interest.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lepitre</LastName><ForeName>T</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Laboratoire de Chimie, URCOM, EA 3221, INC3M CNRS FR-3038, Normandie Université (Université du Havre), UFR des Sciences et Techniques de l'Université du Havre, 25 Rue Philippe Lebon, B.P. 1123, F-76063 Le Havre Cedex, France. lawsona@univ-lehavre.fr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pintiala</LastName><ForeName>C</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Muru</LastName><ForeName>K</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Comesse</LastName><ForeName>S</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Rebbaa</LastName><ForeName>A</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Lawson</LastName><ForeName>A M</ForeName><Initials>AM</Initials></Author><Author ValidYN="Y"><LastName>Daïch</LastName><ForeName>A</ForeName><Initials>A</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>Mar</Month><Day>15</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Org Biomol Chem</MedlineTA><NlmUniqueID>101154995</NlmUniqueID><ISSNLinking>1477-0520</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>3</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>3</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>3</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26976735</ArticleId><ArticleId IdType="doi">10.1039/c6ob00303f</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement></list><tree><noCountry><name sortKey="Comesse, S" sort="Comesse, S" uniqKey="Comesse S" first="S" last="Comesse">S. Comesse</name><name sortKey="Daich, A" sort="Daich, A" uniqKey="Daich A" first="A" last="Daïch">A. Daïch</name><name sortKey="Lawson, A M" sort="Lawson, A M" uniqKey="Lawson A" first="A M" last="Lawson">A M Lawson</name><name sortKey="Muru, K" sort="Muru, K" uniqKey="Muru K" first="K" last="Muru">K. Muru</name><name sortKey="Pintiala, C" sort="Pintiala, C" uniqKey="Pintiala C" first="C" last="Pintiala">C. Pintiala</name><name sortKey="Rebbaa, A" sort="Rebbaa, A" uniqKey="Rebbaa A" first="A" last="Rebbaa">A. Rebbaa</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Lepitre, T" sort="Lepitre, T" uniqKey="Lepitre T" first="T" last="Lepitre">T. Lepitre</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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