Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions
A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C–N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodol...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2014-04, Vol.16 (7), p.1840-1843 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1843 |
|---|---|
| container_issue | 7 |
| container_start_page | 1840 |
| container_title | Organic letters |
| container_volume | 16 |
| creator | Zhu, Chongwei Yi, Meiling Wei, Donghui Chen, Xuan Wu, Yangjie Cui, Xiuling |
| description | A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C–N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions. |
| doi_str_mv | 10.1021/ol500183w |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1513053879</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1513053879</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-7bf35d5887f3b23adfb0090619bb521d811b797edb6bd39d50603ed9ef930bb33</originalsourceid><addsrcrecordid>eNptkE1OwzAQhS0EolBYcAHkDRIsAnaME2dZwk-RChUSrCM7diRXiR3spFBWvQLihj0JqVK6YjWjN9886T0ATjC6xCjEV7akCGFGPnbAAaYhCWJEw93tHqEBOPR-1jGdkuyDQXgdhQwxfAB0autauSDlDS8XX0rCW-1U3sBRpQ1vtDXQFvCl1caW2ij4vFp-Tz-1VB7ONYfpavkzhjfWSDjKGz3vP1ojlYNPupQw7U56LfojsFfw0qvjzRyCt_u713QcTKYPj-loEnDCcBPEoiBUUsbigoiQcFkIhBIU4UQIGmLJMBZxEispIiFJImkXjyiZqCIhSAhChuC8962dfW-Vb7JK-1yVJTfKtj7DFBNECYuTDr3o0dxZ750qstrpirtFhlG2bjbbNtuxpxvbVlRKbsm_KjvgrAd47rOZbZ3pUv5j9AsYyIFU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1513053879</pqid></control><display><type>article</type><title>Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions</title><source>ACS Publications</source><source>MEDLINE</source><creator>Zhu, Chongwei ; Yi, Meiling ; Wei, Donghui ; Chen, Xuan ; Wu, Yangjie ; Cui, Xiuling</creator><creatorcontrib>Zhu, Chongwei ; Yi, Meiling ; Wei, Donghui ; Chen, Xuan ; Wu, Yangjie ; Cui, Xiuling</creatorcontrib><description>A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C–N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol500183w</identifier><identifier>PMID: 24628081</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amination ; Aminoquinolines - chemical synthesis ; Aminoquinolines - chemistry ; Catalysis ; Copper - chemistry ; Molecular Structure ; Oxides - chemistry</subject><ispartof>Organic letters, 2014-04, Vol.16 (7), p.1840-1843</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-7bf35d5887f3b23adfb0090619bb521d811b797edb6bd39d50603ed9ef930bb33</citedby><cites>FETCH-LOGICAL-a381t-7bf35d5887f3b23adfb0090619bb521d811b797edb6bd39d50603ed9ef930bb33</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/ol500183w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol500183w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24628081$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhu, Chongwei</creatorcontrib><creatorcontrib>Yi, Meiling</creatorcontrib><creatorcontrib>Wei, Donghui</creatorcontrib><creatorcontrib>Chen, Xuan</creatorcontrib><creatorcontrib>Wu, Yangjie</creatorcontrib><creatorcontrib>Cui, Xiuling</creatorcontrib><title>Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C–N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.</description><subject>Amination</subject><subject>Aminoquinolines - chemical synthesis</subject><subject>Aminoquinolines - chemistry</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Molecular Structure</subject><subject>Oxides - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1OwzAQhS0EolBYcAHkDRIsAnaME2dZwk-RChUSrCM7diRXiR3spFBWvQLihj0JqVK6YjWjN9886T0ATjC6xCjEV7akCGFGPnbAAaYhCWJEw93tHqEBOPR-1jGdkuyDQXgdhQwxfAB0autauSDlDS8XX0rCW-1U3sBRpQ1vtDXQFvCl1caW2ij4vFp-Tz-1VB7ONYfpavkzhjfWSDjKGz3vP1ojlYNPupQw7U56LfojsFfw0qvjzRyCt_u713QcTKYPj-loEnDCcBPEoiBUUsbigoiQcFkIhBIU4UQIGmLJMBZxEispIiFJImkXjyiZqCIhSAhChuC8962dfW-Vb7JK-1yVJTfKtj7DFBNECYuTDr3o0dxZ750qstrpirtFhlG2bjbbNtuxpxvbVlRKbsm_KjvgrAd47rOZbZ3pUv5j9AsYyIFU</recordid><startdate>20140404</startdate><enddate>20140404</enddate><creator>Zhu, Chongwei</creator><creator>Yi, Meiling</creator><creator>Wei, Donghui</creator><creator>Chen, Xuan</creator><creator>Wu, Yangjie</creator><creator>Cui, Xiuling</creator><general>American Chemical Society</general><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>20140404</creationdate><title>Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions</title><author>Zhu, Chongwei ; Yi, Meiling ; Wei, Donghui ; Chen, Xuan ; Wu, Yangjie ; Cui, Xiuling</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-7bf35d5887f3b23adfb0090619bb521d811b797edb6bd39d50603ed9ef930bb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amination</topic><topic>Aminoquinolines - chemical synthesis</topic><topic>Aminoquinolines - chemistry</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Molecular Structure</topic><topic>Oxides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Chongwei</creatorcontrib><creatorcontrib>Yi, Meiling</creatorcontrib><creatorcontrib>Wei, Donghui</creatorcontrib><creatorcontrib>Chen, Xuan</creatorcontrib><creatorcontrib>Wu, Yangjie</creatorcontrib><creatorcontrib>Cui, Xiuling</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Chongwei</au><au>Yi, Meiling</au><au>Wei, Donghui</au><au>Chen, Xuan</au><au>Wu, Yangjie</au><au>Cui, Xiuling</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2014-04-04</date><risdate>2014</risdate><volume>16</volume><issue>7</issue><spage>1840</spage><epage>1843</epage><pages>1840-1843</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C–N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24628081</pmid><doi>10.1021/ol500183w</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2014-04, Vol.16 (7), p.1840-1843 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1513053879 |
| source | ACS Publications; MEDLINE |
| subjects | Amination Aminoquinolines - chemical synthesis Aminoquinolines - chemistry Catalysis Copper - chemistry Molecular Structure Oxides - chemistry |
| title | Copper-Catalyzed Direct Amination of Quinoline N‑Oxides via C–H Bond Activation under Mild Conditions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T09%3A19%3A26IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper-Catalyzed%20Direct%20Amination%20of%20Quinoline%20N%E2%80%91Oxides%20via%20C%E2%80%93H%20Bond%20Activation%20under%20Mild%20Conditions&rft.jtitle=Organic%20letters&rft.au=Zhu,%20Chongwei&rft.date=2014-04-04&rft.volume=16&rft.issue=7&rft.spage=1840&rft.epage=1843&rft.pages=1840-1843&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol500183w&rft_dat=%3Cproquest_cross%3E1513053879%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1513053879&rft_id=info:pmid/24628081&rfr_iscdi=true |