Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones
The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of...
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| Veröffentlicht in: | Journal of organic chemistry 2011-07, Vol.76 (13), p.5346-5353 |
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| container_end_page | 5353 |
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| container_issue | 13 |
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| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Zhou, Fengtao Liu, Jianguang Ding, Ke Liu, Jinsong Cai, Qian |
| description | The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of isocyanides with triple bonds. Intramolecular trapping of the organocopper intermediates can lead to aryl C–C bond formation, which offered an efficient method for constructing fused pyrrole structures. |
| doi_str_mv | 10.1021/jo2006939 |
| format | Article |
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Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of isocyanides with triple bonds. Intramolecular trapping of the organocopper intermediates can lead to aryl C–C bond formation, which offered an efficient method for constructing fused pyrrole structures.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo2006939</identifier><identifier>PMID: 21591728</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-Quinolones - chemical synthesis ; 4-Quinolones - chemistry ; Amides - chemistry ; Catalysis ; Chemistry ; Copper - chemistry ; Cyanides - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2011-07, Vol.76 (13), p.5346-5353</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-9b328abfc28ac605eeb369168dd79089e13871232104cd1d78dfb0325b5bb5233</citedby><cites>FETCH-LOGICAL-a344t-9b328abfc28ac605eeb369168dd79089e13871232104cd1d78dfb0325b5bb5233</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/jo2006939$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo2006939$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24293485$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21591728$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Fengtao</creatorcontrib><creatorcontrib>Liu, Jianguang</creatorcontrib><creatorcontrib>Ding, Ke</creatorcontrib><creatorcontrib>Liu, Jinsong</creatorcontrib><creatorcontrib>Cai, Qian</creatorcontrib><title>Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of isocyanides with triple bonds. Intramolecular trapping of the organocopper intermediates can lead to aryl C–C bond formation, which offered an efficient method for constructing fused pyrrole structures.</description><subject>4-Quinolones - chemical synthesis</subject><subject>4-Quinolones - chemistry</subject><subject>Amides - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Copper - chemistry</subject><subject>Cyanides - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9P2zAYBnBr2jRK4bAvMOUyARLe_CdO4iOqGFRC28TKCaHIsR1h5NipnQhl131xXCj0gg9-Lz899vsA8AWj7xgR_OPBE4QKTvkHMMOMIFhwlH8EM4QIgZQUdA_sx_iA0mGMfQZ7BDOOS1LNwP-F73sd4EIMwk7_tMpWwindZddayMF4l_k2W0YvJ-GM0jF7NMN99gseE3gprBdhsid98L3xVnTPoPUhG-519ndyaUQTNwl_phC89bf0lEB5tx6N89Y4mEPvdDwAn1phoz7czjm4-Xm-WlzCq98Xy8XZFRQ0zwfIG0oq0bQy3bJATOuGFhwXlVIlRxXXmFYlJpRglEuFVVmptkGUsIY1DSOUzsHRS2768HrUcag7E6W2Vjjtx1hXJS1RgfKNPHmRMvgYg27rPpguLVtjVG8qr98qT_brNnVsOq3e5GvHCXzbAhGlsG0QTpq4cznhNK_YzgkZU_4YXCrjnQefAJ8-lGQ</recordid><startdate>20110701</startdate><enddate>20110701</enddate><creator>Zhou, Fengtao</creator><creator>Liu, Jianguang</creator><creator>Ding, Ke</creator><creator>Liu, Jinsong</creator><creator>Cai, Qian</creator><general>American Chemical Society</general><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>20110701</creationdate><title>Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones</title><author>Zhou, Fengtao ; Liu, Jianguang ; Ding, Ke ; Liu, Jinsong ; Cai, Qian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-9b328abfc28ac605eeb369168dd79089e13871232104cd1d78dfb0325b5bb5233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>4-Quinolones - chemical synthesis</topic><topic>4-Quinolones - chemistry</topic><topic>Amides - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Copper - chemistry</topic><topic>Cyanides - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Fengtao</creatorcontrib><creatorcontrib>Liu, Jianguang</creatorcontrib><creatorcontrib>Ding, Ke</creatorcontrib><creatorcontrib>Liu, Jinsong</creatorcontrib><creatorcontrib>Cai, Qian</creatorcontrib><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>Zhou, Fengtao</au><au>Liu, Jianguang</au><au>Ding, Ke</au><au>Liu, Jinsong</au><au>Cai, Qian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-07-01</date><risdate>2011</risdate><volume>76</volume><issue>13</issue><spage>5346</spage><epage>5353</epage><pages>5346-5353</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of isocyanides with triple bonds. Intramolecular trapping of the organocopper intermediates can lead to aryl C–C bond formation, which offered an efficient method for constructing fused pyrrole structures.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21591728</pmid><doi>10.1021/jo2006939</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2011-07, Vol.76 (13), p.5346-5353 |
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| source | MEDLINE; ACS Publications |
| subjects | 4-Quinolones - chemical synthesis 4-Quinolones - chemistry Amides - chemistry Catalysis Chemistry Copper - chemistry Cyanides - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Molecular Structure Organic chemistry Preparations and properties Stereoisomerism |
| title | Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones |
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