Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones
A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and atmospheric pressure CO2 was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4‐aryl‐2‐quinolinones in moderate to good yields. Notably, a wide range of functional group...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2016-12, Vol.22 (52), p.18729-18732 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 18732 |
|---|---|
| container_issue | 52 |
| container_start_page | 18729 |
| container_title | Chemistry : a European journal |
| container_volume | 22 |
| creator | Sun, Song Hu, Wei-Ming Gu, Ning Cheng, Jiang |
| description | A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and atmospheric pressure CO2 was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4‐aryl‐2‐quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.
Three become one: A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and CO2 at atmospheric pressure was developed whereby a tandem carbene migration insertion/lactamization strategy to afford 4‐aryl‐2‐quinolinones could be isolated in moderate to good yields (see scheme). This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles. |
| doi_str_mv | 10.1002/chem.201604256 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_wiley</sourceid><recordid>TN_cdi_proquest_miscellaneous_1835684282</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1835684282</sourcerecordid><originalsourceid>FETCH-LOGICAL-g3376-68ad1007d72665e335d3e8337702393d52a11f782e7832527105322e6a51e9f63</originalsourceid><addsrcrecordid>eNpdkc1rGzEQxUVoIW7aa86CXnKoEmlkSatjWPJFPlyXhByFsORGiXblrnaxN399ZRx8yGkY5vceb3gIHTN6yiiFs8WLb06BMkmnIOQBmjABjHAlxRc0oXqqiBRcH6JvOb9SSrXkfII2v22M1oWhIbXtbRzfvcP3Q-wDqVOzSq1ve_zH20UfUptxWuIH8pjyGF9G19n3cs-_MJCb5JJtQwxlx7Z1uJ4B7tPadi7jKTnvxkiAzIfQpsJsVd_R16WN2f_4mEfo6fLisb4md7Orm_r8jvzlJTqRlXXlO-UUSCk858JxX5WTosA1dwIsY0tVgVcVBwGKUcEBvLSCeb2U_Aid7HxXXfo3-NybJuSFL0-3Pg3ZsIoLWU2hgoL-_IS-pqFrS7pCCdBagdoa6h21DtGPZtWFxnajYdRsWzDbFsy-BVNfX9zvt6IlO23Ivd_stbZ7M1JxJczzw5VRt3OoniUYzf8DkVyKwg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1852997276</pqid></control><display><type>article</type><title>Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Sun, Song ; Hu, Wei-Ming ; Gu, Ning ; Cheng, Jiang</creator><creatorcontrib>Sun, Song ; Hu, Wei-Ming ; Gu, Ning ; Cheng, Jiang</creatorcontrib><description>A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and atmospheric pressure CO2 was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4‐aryl‐2‐quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.
Three become one: A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and CO2 at atmospheric pressure was developed whereby a tandem carbene migration insertion/lactamization strategy to afford 4‐aryl‐2‐quinolinones could be isolated in moderate to good yields (see scheme). This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201604256</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>4-aryl-2-quinolinone ; carbon dioxide fixation ; Chemistry ; heterocycles ; multi-component reaction ; N-tosylhydrazone</subject><ispartof>Chemistry : a European journal, 2016-12, Vol.22 (52), p.18729-18732</ispartof><rights>2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201604256$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201604256$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Sun, Song</creatorcontrib><creatorcontrib>Hu, Wei-Ming</creatorcontrib><creatorcontrib>Gu, Ning</creatorcontrib><creatorcontrib>Cheng, Jiang</creatorcontrib><title>Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and atmospheric pressure CO2 was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4‐aryl‐2‐quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.
Three become one: A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and CO2 at atmospheric pressure was developed whereby a tandem carbene migration insertion/lactamization strategy to afford 4‐aryl‐2‐quinolinones could be isolated in moderate to good yields (see scheme). This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.</description><subject>4-aryl-2-quinolinone</subject><subject>carbon dioxide fixation</subject><subject>Chemistry</subject><subject>heterocycles</subject><subject>multi-component reaction</subject><subject>N-tosylhydrazone</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNpdkc1rGzEQxUVoIW7aa86CXnKoEmlkSatjWPJFPlyXhByFsORGiXblrnaxN399ZRx8yGkY5vceb3gIHTN6yiiFs8WLb06BMkmnIOQBmjABjHAlxRc0oXqqiBRcH6JvOb9SSrXkfII2v22M1oWhIbXtbRzfvcP3Q-wDqVOzSq1ve_zH20UfUptxWuIH8pjyGF9G19n3cs-_MJCb5JJtQwxlx7Z1uJ4B7tPadi7jKTnvxkiAzIfQpsJsVd_R16WN2f_4mEfo6fLisb4md7Orm_r8jvzlJTqRlXXlO-UUSCk858JxX5WTosA1dwIsY0tVgVcVBwGKUcEBvLSCeb2U_Aid7HxXXfo3-NybJuSFL0-3Pg3ZsIoLWU2hgoL-_IS-pqFrS7pCCdBagdoa6h21DtGPZtWFxnajYdRsWzDbFsy-BVNfX9zvt6IlO23Ivd_stbZ7M1JxJczzw5VRt3OoniUYzf8DkVyKwg</recordid><startdate>20161223</startdate><enddate>20161223</enddate><creator>Sun, Song</creator><creator>Hu, Wei-Ming</creator><creator>Gu, Ning</creator><creator>Cheng, Jiang</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20161223</creationdate><title>Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones</title><author>Sun, Song ; Hu, Wei-Ming ; Gu, Ning ; Cheng, Jiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g3376-68ad1007d72665e335d3e8337702393d52a11f782e7832527105322e6a51e9f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>4-aryl-2-quinolinone</topic><topic>carbon dioxide fixation</topic><topic>Chemistry</topic><topic>heterocycles</topic><topic>multi-component reaction</topic><topic>N-tosylhydrazone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Song</creatorcontrib><creatorcontrib>Hu, Wei-Ming</creatorcontrib><creatorcontrib>Gu, Ning</creatorcontrib><creatorcontrib>Cheng, Jiang</creatorcontrib><collection>Istex</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Song</au><au>Hu, Wei-Ming</au><au>Gu, Ning</au><au>Cheng, Jiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-12-23</date><risdate>2016</risdate><volume>22</volume><issue>52</issue><spage>18729</spage><epage>18732</epage><pages>18729-18732</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and atmospheric pressure CO2 was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4‐aryl‐2‐quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.
Three become one: A palladium‐catalyzed three‐component reaction between N‐tosylhydrazones, 2‐iodoanilines and CO2 at atmospheric pressure was developed whereby a tandem carbene migration insertion/lactamization strategy to afford 4‐aryl‐2‐quinolinones could be isolated in moderate to good yields (see scheme). This protocol features the simultaneous formation of four novel bonds; two C−C, one C=C and one C−N (amide), representing an efficient methodology for incorporation of CO2 into heterocycles.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/chem.201604256</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2016-12, Vol.22 (52), p.18729-18732 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1835684282 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 4-aryl-2-quinolinone carbon dioxide fixation Chemistry heterocycles multi-component reaction N-tosylhydrazone |
| title | Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2 towards 4-Aryl-2-Quinolinones |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-16T06%3A42%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_wiley&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Palladium-Catalyzed%20Multi-Component%20Reactions%20of%20N-Tosylhydrazones,%202-Iodoanilines%20and%20CO2%20towards%204-Aryl-2-Quinolinones&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Sun,%20Song&rft.date=2016-12-23&rft.volume=22&rft.issue=52&rft.spage=18729&rft.epage=18732&rft.pages=18729-18732&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201604256&rft_dat=%3Cproquest_wiley%3E1835684282%3C/proquest_wiley%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1852997276&rft_id=info:pmid/&rfr_iscdi=true |