I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides
An efficient and alternative isatin‐to‐quinoline strategy illustrates the metal‐like behavior of molecular iodine in the N−O reduction of ketoxime acetates. This process involves N−O/C−N bond cleavages and C−C/C−N bond formation to furnish pharmacologically significant quinoline‐4‐carboxamide deriva...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2018-04, Vol.360 (7), p.1364-1369 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1369 |
|---|---|
| container_issue | 7 |
| container_start_page | 1364 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 360 |
| creator | Gao, Qinghe Liu, Zhaomin Wang, Yakun Wu, Xia Zhang, Jixia Wu, Anxin |
| description | An efficient and alternative isatin‐to‐quinoline strategy illustrates the metal‐like behavior of molecular iodine in the N−O reduction of ketoxime acetates. This process involves N−O/C−N bond cleavages and C−C/C−N bond formation to furnish pharmacologically significant quinoline‐4‐carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single‐electron reduction coupling reactions in a manner similar to transition metals.
magnified image |
| doi_str_mv | 10.1002/adsc.201701610 |
| format | Article |
| fullrecord | <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1002_adsc_201701610</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1002_adsc_201701610</sourcerecordid><originalsourceid>FETCH-LOGICAL-c169t-1f90182d412e12d7156537abf767db3b56f8fec8bd4b2ff215149e8ebf501bc23</originalsourceid><addsrcrecordid>eNo9kM1OAjEQxxujiYhePfcFFjvdjy7eCFHYhPiBeN7stlOsga5piwk3H0Ff0SexgOEyM4dffjPzJ-Qa2AAY4zeN8nLAGQgGBbAT0ostTzIohqfHOWfn5ML7dxaxUoge-akop79f3wtnlkt0qOgc1UYG84l0ghZdE0xnaafpQ6TGaMMeqtbGbld03igjm5W_pSNLKx9ZG6nQxfK8MbZbGYv0JUQJLrdUd46GN6SVDa7bLzmYn5xZN25LR2uj0F-SMx2VePXf--T1_m4xniazx0k1Hs0SGT8KCeghg5KrDDgCVwLyIk9F02pRCNWmbV7oUqMsW5W1XGsOOWRDLLHVOYNW8rRPBgevdJ33DnX9cbijBlbvAq13gdbHQNM_7g1vTA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides</title><source>Access via Wiley Online Library</source><creator>Gao, Qinghe ; Liu, Zhaomin ; Wang, Yakun ; Wu, Xia ; Zhang, Jixia ; Wu, Anxin</creator><creatorcontrib>Gao, Qinghe ; Liu, Zhaomin ; Wang, Yakun ; Wu, Xia ; Zhang, Jixia ; Wu, Anxin</creatorcontrib><description>An efficient and alternative isatin‐to‐quinoline strategy illustrates the metal‐like behavior of molecular iodine in the N−O reduction of ketoxime acetates. This process involves N−O/C−N bond cleavages and C−C/C−N bond formation to furnish pharmacologically significant quinoline‐4‐carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single‐electron reduction coupling reactions in a manner similar to transition metals.
magnified image</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201701610</identifier><language>eng</language><ispartof>Advanced synthesis & catalysis, 2018-04, Vol.360 (7), p.1364-1369</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c169t-1f90182d412e12d7156537abf767db3b56f8fec8bd4b2ff215149e8ebf501bc23</citedby><cites>FETCH-LOGICAL-c169t-1f90182d412e12d7156537abf767db3b56f8fec8bd4b2ff215149e8ebf501bc23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27926,27927</link.rule.ids></links><search><creatorcontrib>Gao, Qinghe</creatorcontrib><creatorcontrib>Liu, Zhaomin</creatorcontrib><creatorcontrib>Wang, Yakun</creatorcontrib><creatorcontrib>Wu, Xia</creatorcontrib><creatorcontrib>Zhang, Jixia</creatorcontrib><creatorcontrib>Wu, Anxin</creatorcontrib><title>I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides</title><title>Advanced synthesis & catalysis</title><description>An efficient and alternative isatin‐to‐quinoline strategy illustrates the metal‐like behavior of molecular iodine in the N−O reduction of ketoxime acetates. This process involves N−O/C−N bond cleavages and C−C/C−N bond formation to furnish pharmacologically significant quinoline‐4‐carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single‐electron reduction coupling reactions in a manner similar to transition metals.
magnified image</description><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNo9kM1OAjEQxxujiYhePfcFFjvdjy7eCFHYhPiBeN7stlOsga5piwk3H0Ff0SexgOEyM4dffjPzJ-Qa2AAY4zeN8nLAGQgGBbAT0ostTzIohqfHOWfn5ML7dxaxUoge-akop79f3wtnlkt0qOgc1UYG84l0ghZdE0xnaafpQ6TGaMMeqtbGbld03igjm5W_pSNLKx9ZG6nQxfK8MbZbGYv0JUQJLrdUd46GN6SVDa7bLzmYn5xZN25LR2uj0F-SMx2VePXf--T1_m4xniazx0k1Hs0SGT8KCeghg5KrDDgCVwLyIk9F02pRCNWmbV7oUqMsW5W1XGsOOWRDLLHVOYNW8rRPBgevdJ33DnX9cbijBlbvAq13gdbHQNM_7g1vTA</recordid><startdate>20180403</startdate><enddate>20180403</enddate><creator>Gao, Qinghe</creator><creator>Liu, Zhaomin</creator><creator>Wang, Yakun</creator><creator>Wu, Xia</creator><creator>Zhang, Jixia</creator><creator>Wu, Anxin</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20180403</creationdate><title>I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides</title><author>Gao, Qinghe ; Liu, Zhaomin ; Wang, Yakun ; Wu, Xia ; Zhang, Jixia ; Wu, Anxin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c169t-1f90182d412e12d7156537abf767db3b56f8fec8bd4b2ff215149e8ebf501bc23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gao, Qinghe</creatorcontrib><creatorcontrib>Liu, Zhaomin</creatorcontrib><creatorcontrib>Wang, Yakun</creatorcontrib><creatorcontrib>Wu, Xia</creatorcontrib><creatorcontrib>Zhang, Jixia</creatorcontrib><creatorcontrib>Wu, Anxin</creatorcontrib><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gao, Qinghe</au><au>Liu, Zhaomin</au><au>Wang, Yakun</au><au>Wu, Xia</au><au>Zhang, Jixia</au><au>Wu, Anxin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-04-03</date><risdate>2018</risdate><volume>360</volume><issue>7</issue><spage>1364</spage><epage>1369</epage><pages>1364-1369</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An efficient and alternative isatin‐to‐quinoline strategy illustrates the metal‐like behavior of molecular iodine in the N−O reduction of ketoxime acetates. This process involves N−O/C−N bond cleavages and C−C/C−N bond formation to furnish pharmacologically significant quinoline‐4‐carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single‐electron reduction coupling reactions in a manner similar to transition metals.
magnified image</abstract><doi>10.1002/adsc.201701610</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2018-04, Vol.360 (7), p.1364-1369 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_adsc_201701610 |
| source | Access via Wiley Online Library |
| title | I 2 ‐Triggered Reductive Generation of N‐Centered Iminyl Radicals: An Isatin‐to‐Quinoline Strategy for the Introduction of Primary Amides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T08%3A44%3A36IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=I%202%20%E2%80%90Triggered%20Reductive%20Generation%20of%20N%E2%80%90Centered%20Iminyl%20Radicals:%20An%20Isatin%E2%80%90to%E2%80%90Quinoline%20Strategy%20for%20the%20Introduction%20of%20Primary%20Amides&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Gao,%20Qinghe&rft.date=2018-04-03&rft.volume=360&rft.issue=7&rft.spage=1364&rft.epage=1369&rft.pages=1364-1369&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201701610&rft_dat=%3Ccrossref%3E10_1002_adsc_201701610%3C/crossref%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |