Synthesis of Quinolines from 3-Formylchromone
A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible...
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| Veröffentlicht in: | Journal of organic chemistry 2008-08, Vol.73 (15), p.6010-6013 |
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| container_end_page | 6013 |
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| container_issue | 15 |
| container_start_page | 6010 |
| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Plaskon, Andrey S Ryabukhin, Sergey V Volochnyuk, Dmitriy M Gavrilenko, Konstantin S Shivanyuk, Alexander N Tolmachev, Andrey A |
| description | A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible mechanism for the heterocyclizations was proposed. |
| doi_str_mv | 10.1021/jo800950y |
| format | Article |
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Limitations and scope of this methodology were established, and a possible mechanism for the heterocyclizations was proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo800950y</identifier><identifier>PMID: 18593188</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Chromones - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Kinetics and mechanisms ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Reactivity and mechanisms</subject><ispartof>Journal of organic chemistry, 2008-08, Vol.73 (15), p.6010-6013</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-5e6c52f5140d4623505ebc471ee04e0f57acba5db4590c565e6f5cdf1383cbbc3</citedby><cites>FETCH-LOGICAL-a381t-5e6c52f5140d4623505ebc471ee04e0f57acba5db4590c565e6f5cdf1383cbbc3</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/jo800950y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo800950y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20531967$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18593188$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Plaskon, Andrey S</creatorcontrib><creatorcontrib>Ryabukhin, Sergey V</creatorcontrib><creatorcontrib>Volochnyuk, Dmitriy M</creatorcontrib><creatorcontrib>Gavrilenko, Konstantin S</creatorcontrib><creatorcontrib>Shivanyuk, Alexander N</creatorcontrib><creatorcontrib>Tolmachev, Andrey A</creatorcontrib><title>Synthesis of Quinolines from 3-Formylchromone</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A facile and versatile procedure for the synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones was elaborated on the basis of TMSCl-mediated recyclization of 3-formylchromone with various anilines. Limitations and scope of this methodology were established, and a possible mechanism for the heterocyclizations was proposed.</description><subject>Chemistry</subject><subject>Chromones - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Kinetics and mechanisms</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9LwzAUB_AgipvTg_-A7KLgofrS9PXHUYabwlDH5mWXkKYJ62ybmazg_nsjK9vFXB7hffjy-BJyTeGBQkgf1yYFyBB2J6RPMYQgziA6JX2AMAxYGLMeuXBuDf4h4jnp0RQzRtO0T4L5rtmulCvd0OjhrC0bU5WNckNtTT1kwdjYelfJlf-ZRl2SMy0qp666OSCf4-fF6CWYvk9eR0_TQLCUbgNUscRQI42giOKQIaDKZZRQpSBSoDERMhdY5BFmIDH2XqMsNGUpk3ku2YDc7XM31ny3ym15XTqpqko0yrSOx5nPjBPq4f0eSmucs0rzjS1rYXecAv_rhh-68famC23zWhVH2ZXhwW0HhJOi0lY0snQHFwIymsWJd8HelW6rfg57Yb-43ybIFx9z_jbJ2IwuU7485grp_D2tbXx3_xz4C879hig</recordid><startdate>20080801</startdate><enddate>20080801</enddate><creator>Plaskon, Andrey S</creator><creator>Ryabukhin, Sergey V</creator><creator>Volochnyuk, Dmitriy M</creator><creator>Gavrilenko, Konstantin S</creator><creator>Shivanyuk, Alexander N</creator><creator>Tolmachev, Andrey A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>20080801</creationdate><title>Synthesis of Quinolines from 3-Formylchromone</title><author>Plaskon, Andrey S ; Ryabukhin, Sergey V ; Volochnyuk, Dmitriy M ; Gavrilenko, Konstantin S ; Shivanyuk, Alexander N ; Tolmachev, Andrey A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-5e6c52f5140d4623505ebc471ee04e0f57acba5db4590c565e6f5cdf1383cbbc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Chemistry</topic><topic>Chromones - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Kinetics and mechanisms</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Plaskon, Andrey S</creatorcontrib><creatorcontrib>Ryabukhin, Sergey V</creatorcontrib><creatorcontrib>Volochnyuk, Dmitriy M</creatorcontrib><creatorcontrib>Gavrilenko, Konstantin S</creatorcontrib><creatorcontrib>Shivanyuk, Alexander N</creatorcontrib><creatorcontrib>Tolmachev, Andrey A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Plaskon, Andrey S</au><au>Ryabukhin, Sergey V</au><au>Volochnyuk, Dmitriy M</au><au>Gavrilenko, Konstantin S</au><au>Shivanyuk, Alexander N</au><au>Tolmachev, Andrey A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Quinolines from 3-Formylchromone</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2008-08, Vol.73 (15), p.6010-6013 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69350671 |
| source | MEDLINE; ACS Publications |
| subjects | Chemistry Chromones - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Molecular Structure Organic chemistry Preparations and properties Quinolines - chemical synthesis Quinolines - chemistry Reactivity and mechanisms |
| title | Synthesis of Quinolines from 3-Formylchromone |
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