Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines
α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the pr...
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| Veröffentlicht in: | Organic letters 2000-07, Vol.2 (15), p.2339-2341 |
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| container_issue | 15 |
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| container_title | Organic letters |
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| creator | Marcoux, Jean-François Corley, Edward G Rossen, Kai Pye, Phil Wu, Jimmy Robbins, Michael A Davies, Ian W Larsen, Robert D Reider, Paul J |
| description | α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues. |
| doi_str_mv | 10.1021/ol006097b |
| format | Article |
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The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol006097b</identifier><identifier>PMID: 10930278</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cyclooxygenase Inhibitors - chemical synthesis ; Cyclooxygenase Inhibitors - chemistry ; Cyclooxygenase Inhibitors - metabolism ; Fluorides - chemistry ; Fluorides - metabolism ; Ketones - chemistry ; Ketones - metabolism ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - metabolism</subject><ispartof>Organic letters, 2000-07, Vol.2 (15), p.2339-2341</ispartof><rights>Copyright © 2000 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-6d212d553c571d0241c50c3cbf6b1261ce5e62521f9dff7cbc22c2eff4f86b183</citedby><cites>FETCH-LOGICAL-a311t-6d212d553c571d0241c50c3cbf6b1261ce5e62521f9dff7cbc22c2eff4f86b183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol006097b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol006097b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10930278$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Marcoux, Jean-François</creatorcontrib><creatorcontrib>Corley, Edward G</creatorcontrib><creatorcontrib>Rossen, Kai</creatorcontrib><creatorcontrib>Pye, Phil</creatorcontrib><creatorcontrib>Wu, Jimmy</creatorcontrib><creatorcontrib>Robbins, Michael A</creatorcontrib><creatorcontrib>Davies, Ian W</creatorcontrib><creatorcontrib>Larsen, Robert D</creatorcontrib><creatorcontrib>Reider, Paul J</creatorcontrib><title>Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.</description><subject>Cyclooxygenase Inhibitors - chemical synthesis</subject><subject>Cyclooxygenase Inhibitors - chemistry</subject><subject>Cyclooxygenase Inhibitors - metabolism</subject><subject>Fluorides - chemistry</subject><subject>Fluorides - metabolism</subject><subject>Ketones - chemistry</subject><subject>Ketones - metabolism</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - metabolism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKxDAUhoMoXkYXvoBko-CimqSmnbobhvGCgoKXbUnTEybSJjUXvKzc-po-iR06DC48m3P4-fjg_AjtU3JCCaOntiEkI0VeraFtylma5ISz9dWdkS204_0LIbRPik20RUmREpaPt9HnxJjYiKCtwVbhGwjWgMdvOszxszai1bU2Orb4Ct6FaqJ1tptb381FAPwgmuDPf76-8cTgmVJaajAB3zvohFs5H532sfJBhxigxvcfbuEEv4s2lGg87C33CD1dzB6nV8nt3eX1dHKbiJTSkGQ1o6zmPJU8pzVhZ1RyIlNZqayiLKMSOGSMM6qKWqlcVpIxyUCpMzXuiXE6QkeDt3P2NYIPZau9hKYRBmz0ZU7zlKf9jNDxAEpnvXegys7pVriPkpJyUXS5KrpnD5bSWLVQ_yGHZnvgcACE9OWLjc70P_4j-gVtQIgh</recordid><startdate>20000727</startdate><enddate>20000727</enddate><creator>Marcoux, Jean-François</creator><creator>Corley, Edward G</creator><creator>Rossen, Kai</creator><creator>Pye, Phil</creator><creator>Wu, Jimmy</creator><creator>Robbins, Michael A</creator><creator>Davies, Ian W</creator><creator>Larsen, Robert D</creator><creator>Reider, Paul J</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20000727</creationdate><title>Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines</title><author>Marcoux, Jean-François ; Corley, Edward G ; Rossen, Kai ; Pye, Phil ; Wu, Jimmy ; Robbins, Michael A ; Davies, Ian W ; Larsen, Robert D ; Reider, Paul J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-6d212d553c571d0241c50c3cbf6b1261ce5e62521f9dff7cbc22c2eff4f86b183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Cyclooxygenase Inhibitors - chemical synthesis</topic><topic>Cyclooxygenase Inhibitors - chemistry</topic><topic>Cyclooxygenase Inhibitors - metabolism</topic><topic>Fluorides - chemistry</topic><topic>Fluorides - metabolism</topic><topic>Ketones - chemistry</topic><topic>Ketones - metabolism</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marcoux, Jean-François</creatorcontrib><creatorcontrib>Corley, Edward G</creatorcontrib><creatorcontrib>Rossen, Kai</creatorcontrib><creatorcontrib>Pye, Phil</creatorcontrib><creatorcontrib>Wu, Jimmy</creatorcontrib><creatorcontrib>Robbins, Michael A</creatorcontrib><creatorcontrib>Davies, Ian W</creatorcontrib><creatorcontrib>Larsen, Robert D</creatorcontrib><creatorcontrib>Reider, Paul J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marcoux, Jean-François</au><au>Corley, Edward G</au><au>Rossen, Kai</au><au>Pye, Phil</au><au>Wu, Jimmy</au><au>Robbins, Michael A</au><au>Davies, Ian W</au><au>Larsen, Robert D</au><au>Reider, Paul J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2000-07, Vol.2 (15), p.2339-2341 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Cyclooxygenase Inhibitors - chemical synthesis Cyclooxygenase Inhibitors - chemistry Cyclooxygenase Inhibitors - metabolism Fluorides - chemistry Fluorides - metabolism Ketones - chemistry Ketones - metabolism Pyridines - chemical synthesis Pyridines - chemistry Pyridines - metabolism |
| title | Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines |
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