Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation
Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for t...
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| Veröffentlicht in: | Journal of organic chemistry 2013-02, Vol.78 (3), p.1273-1277 |
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| container_end_page | 1277 |
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| container_issue | 3 |
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| container_title | Journal of organic chemistry |
| container_volume | 78 |
| creator | Li, Bryan Samp, Lacey Sagal, John Hayward, Cheryl M Yang, Christine Zhang, Zhijun |
| description | Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for the syntheses of quinazolin-4(3H)-ones. Thus, reaction of 2-bromo or 2-iodo benzoate esters with amdidines afforded substituted quinazolin-4(3H)-ones in 44–89% yields. |
| doi_str_mv | 10.1021/jo302515c |
| format | Article |
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The amidine arylation method was found applicable for the syntheses of quinazolin-4(3H)-ones. Thus, reaction of 2-bromo or 2-iodo benzoate esters with amdidines afforded substituted quinazolin-4(3H)-ones in 44–89% yields.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo302515c</identifier><identifier>PMID: 23289853</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amidines - chemistry ; Catalysis ; Cyclization ; Hydrocarbons, Halogenated - chemistry ; Molecular Structure ; Nicotinic Acids - chemistry ; Pyrimidinones - chemical synthesis ; Pyrimidinones - chemistry ; Quinazolinones - chemical synthesis ; Quinazolinones - chemistry</subject><ispartof>Journal of organic chemistry, 2013-02, Vol.78 (3), p.1273-1277</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-93ad6a3f350eb19307b18ff3d5f15602b76b8f49adee6ba2d3d3f876cf17dae33</citedby><cites>FETCH-LOGICAL-a315t-93ad6a3f350eb19307b18ff3d5f15602b76b8f49adee6ba2d3d3f876cf17dae33</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/jo302515c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo302515c$$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/23289853$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Bryan</creatorcontrib><creatorcontrib>Samp, Lacey</creatorcontrib><creatorcontrib>Sagal, John</creatorcontrib><creatorcontrib>Hayward, Cheryl M</creatorcontrib><creatorcontrib>Yang, Christine</creatorcontrib><creatorcontrib>Zhang, Zhijun</creatorcontrib><title>Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for the syntheses of quinazolin-4(3H)-ones. Thus, reaction of 2-bromo or 2-iodo benzoate esters with amdidines afforded substituted quinazolin-4(3H)-ones in 44–89% yields.</description><subject>Amidines - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Molecular Structure</subject><subject>Nicotinic Acids - chemistry</subject><subject>Pyrimidinones - chemical synthesis</subject><subject>Pyrimidinones - chemistry</subject><subject>Quinazolinones - chemical synthesis</subject><subject>Quinazolinones - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkNFKwzAUhoMobk4vfAHpjbBdVJOcJW1vhDLUCUMR9bqkTYIZbTKbVphXvoKv6JMY2dyV5-bA4ft_OB9CpwRfEEzJ5dIBpoywag8NCaM45hme7qMhxpTGQDkM0JH3SxyGMXaIBhRomqUMhujqaW27V-WNj5yOHntjxYerjY2nY5hPvj-_nFU-ejciyhsjjVXRfTjm7boWnXH2GB1oUXt1st0j9HJz_Tybx4uH27tZvogFENbFGQjJBWhgWJUkA5yUJNUaJNOEcUzLhJepnmZCKsVLQSVI0GnCK00SKRTACI03vavWvfXKd0VjfKXqWljlel8QmkICNEl5QCcbtGqd963Sxao1jWjXBcHFr65ipyuwZ9vavmyU3JF_fgJwvgFE5UOub2348p-iH1jDcbI</recordid><startdate>20130201</startdate><enddate>20130201</enddate><creator>Li, Bryan</creator><creator>Samp, Lacey</creator><creator>Sagal, John</creator><creator>Hayward, Cheryl M</creator><creator>Yang, Christine</creator><creator>Zhang, Zhijun</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>20130201</creationdate><title>Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation</title><author>Li, Bryan ; Samp, Lacey ; Sagal, John ; Hayward, Cheryl M ; Yang, Christine ; Zhang, Zhijun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-93ad6a3f350eb19307b18ff3d5f15602b76b8f49adee6ba2d3d3f876cf17dae33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Amidines - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Molecular Structure</topic><topic>Nicotinic Acids - chemistry</topic><topic>Pyrimidinones - chemical synthesis</topic><topic>Pyrimidinones - chemistry</topic><topic>Quinazolinones - chemical synthesis</topic><topic>Quinazolinones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Bryan</creatorcontrib><creatorcontrib>Samp, Lacey</creatorcontrib><creatorcontrib>Sagal, John</creatorcontrib><creatorcontrib>Hayward, Cheryl M</creatorcontrib><creatorcontrib>Yang, Christine</creatorcontrib><creatorcontrib>Zhang, Zhijun</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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Bryan</au><au>Samp, Lacey</au><au>Sagal, John</au><au>Hayward, Cheryl M</au><au>Yang, Christine</au><au>Zhang, Zhijun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2013-02-01</date><risdate>2013</risdate><volume>78</volume><issue>3</issue><spage>1273</spage><epage>1277</epage><pages>1273-1277</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for the syntheses of quinazolin-4(3H)-ones. Thus, reaction of 2-bromo or 2-iodo benzoate esters with amdidines afforded substituted quinazolin-4(3H)-ones in 44–89% yields.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23289853</pmid><doi>10.1021/jo302515c</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2013-02, Vol.78 (3), p.1273-1277 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amidines - chemistry Catalysis Cyclization Hydrocarbons, Halogenated - chemistry Molecular Structure Nicotinic Acids - chemistry Pyrimidinones - chemical synthesis Pyrimidinones - chemistry Quinazolinones - chemical synthesis Quinazolinones - chemistry |
| title | Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation |
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