TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient Synthesis of Pyrano- and Furanoquinolines
Abstract An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran...
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| Veröffentlicht in: | Synlett 2006-06, Vol.2006 (9), p.1399-1403 |
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| container_issue | 9 |
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| container_title | Synlett |
| container_volume | 2006 |
| creator | More, Shivaji V. Sastry, M. N. Yao, Ching-Fa |
| description | Abstract
An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction. |
| doi_str_mv | 10.1055/s-2006-939711 |
| format | Article |
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An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-2006-939711</identifier><language>eng</language><subject>letter</subject><ispartof>Synlett, 2006-06, Vol.2006 (9), p.1399-1403</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c274t-eec3d8e59f5884618efc50c7b80be699447c8853bfac9b96e22ceb6f773c22993</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-939711.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2006-939711$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>More, Shivaji V.</creatorcontrib><creatorcontrib>Sastry, M. N.</creatorcontrib><creatorcontrib>Yao, Ching-Fa</creatorcontrib><title>TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient Synthesis of Pyrano- and Furanoquinolines</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract
An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp1kEFOwzAQRS0EEqWwZO8DYLATJ7HZRaEFpCIQLWvLccaqK9cpcbpI78QlOBktZctqvkZPX18PoWtGbxnNsrtIEkpzIlNZMHaCRoynxf4l81M0ojLNSZYwfo4uYlxRyriQdIT84mVeeVLpXvthBw0ud5o8OPCRlL6BDr-DNr1rwz0u8dytNx6wDg2eWOuMg9Dj76_5EPolRBdxa_Hb0OnQkl9ouj3kz60LrXcB4iU6s9pHuPq7Y_QxnSyqJzJ7fXyuyhkxScF7AmDSRkAmbSYEz5kAazJqilrQGnIpOS-MEFlaW21kLXNIEgN1bosiNUkiZTpG5NhrujbGDqzadG6tu0Exqg6qVFQHVeqoas_fHPl-6WANatVuu7Af-A_-A3AXayA</recordid><startdate>20060601</startdate><enddate>20060601</enddate><creator>More, Shivaji V.</creator><creator>Sastry, M. N.</creator><creator>Yao, Ching-Fa</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20060601</creationdate><title>TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient Synthesis of Pyrano- and Furanoquinolines</title><author>More, Shivaji V. ; Sastry, M. N. ; Yao, Ching-Fa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-eec3d8e59f5884618efc50c7b80be699447c8853bfac9b96e22ceb6f773c22993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>More, Shivaji V.</creatorcontrib><creatorcontrib>Sastry, M. N.</creatorcontrib><creatorcontrib>Yao, Ching-Fa</creatorcontrib><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>More, Shivaji V.</au><au>Sastry, M. N.</au><au>Yao, Ching-Fa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient Synthesis of Pyrano- and Furanoquinolines</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2006-06-01</date><risdate>2006</risdate><volume>2006</volume><issue>9</issue><spage>1399</spage><epage>1403</epage><pages>1399-1403</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract
An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.</abstract><doi>10.1055/s-2006-939711</doi><tpages>5</tpages></addata></record> |
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| ispartof | Synlett, 2006-06, Vol.2006 (9), p.1399-1403 |
| issn | 0936-5214 1437-2096 |
| language | eng |
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| source | Thieme Connect Journals |
| subjects | letter |
| title | TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient Synthesis of Pyrano- and Furanoquinolines |
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