Remote Functionalization of 8‐Substituted Quinolines with para‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes
A C(5)−H remote functionalization of 8‐aminoquinoline derivatives with para‐quinone methides, affording direct access to unsymmetrical tri(hetero)arylmethanes in 69–96 % yield is described. This method provides diverse tri(hetero)arylmethanes with a broad scope and in a regioselective manner. The tr...
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| Veröffentlicht in: | European journal of organic chemistry 2022-08, Vol.2022 (32), p.n/a |
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| container_title | European journal of organic chemistry |
| container_volume | 2022 |
| creator | Burra, Amarender G. Uredi, Dilipkumar Motati, Damoder R. Fronczek, Frank R. Watkins, E. Blake |
| description | A C(5)−H remote functionalization of 8‐aminoquinoline derivatives with para‐quinone methides, affording direct access to unsymmetrical tri(hetero)arylmethanes in 69–96 % yield is described. This method provides diverse tri(hetero)arylmethanes with a broad scope and in a regioselective manner. The transformation works well with electron‐rich and electron‐deficient substrates.
An expedient method for the preparation of unsymmetrical tri(hetero)arylmethanes from para‐quinone methides and derivatives of 8‐aminoquinoline under copper catalysis is described. |
| doi_str_mv | 10.1002/ejoc.202200191 |
| format | Article |
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An expedient method for the preparation of unsymmetrical tri(hetero)arylmethanes from para‐quinone methides and derivatives of 8‐aminoquinoline under copper catalysis is described.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202200191</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>8-Aminoquinoline amide ; Alkylation ; Aminoquinolines ; Copper (II) ; Electrophilic addition ; Organic compounds ; Quinones ; Substrates ; Tri(hetero)arylmethanes</subject><ispartof>European journal of organic chemistry, 2022-08, Vol.2022 (32), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3171-cc947d363089f71ff11aca3f3fe428c52ab53098498f7fc81375fde8487f9943</citedby><cites>FETCH-LOGICAL-c3171-cc947d363089f71ff11aca3f3fe428c52ab53098498f7fc81375fde8487f9943</cites><orcidid>0000-0002-7505-0083</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202200191$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202200191$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Burra, Amarender G.</creatorcontrib><creatorcontrib>Uredi, Dilipkumar</creatorcontrib><creatorcontrib>Motati, Damoder R.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Watkins, E. Blake</creatorcontrib><title>Remote Functionalization of 8‐Substituted Quinolines with para‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes</title><title>European journal of organic chemistry</title><description>A C(5)−H remote functionalization of 8‐aminoquinoline derivatives with para‐quinone methides, affording direct access to unsymmetrical tri(hetero)arylmethanes in 69–96 % yield is described. This method provides diverse tri(hetero)arylmethanes with a broad scope and in a regioselective manner. The transformation works well with electron‐rich and electron‐deficient substrates.
An expedient method for the preparation of unsymmetrical tri(hetero)arylmethanes from para‐quinone methides and derivatives of 8‐aminoquinoline under copper catalysis is described.</description><subject>8-Aminoquinoline amide</subject><subject>Alkylation</subject><subject>Aminoquinolines</subject><subject>Copper (II)</subject><subject>Electrophilic addition</subject><subject>Organic compounds</subject><subject>Quinones</subject><subject>Substrates</subject><subject>Tri(hetero)arylmethanes</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhSMEEqWwMltigSHFjtPEZkNVy4-KKqBIbJHrXCuu0rjYjqoyMfAAPCNPgksRjEz36Oqco3u_KDomuEcwTs5hbmQvwUmCMeFkJ-oQzHmMM453g05pGhNOn_ejA-fmGGOeZaQTvT_AwnhAo7aRXptG1PpVbAQyCrHPt4_Hdua89q2HEt23ujG1bsChlfYVWgorguV73QC6A1_pEtwFupQSnEPeoKfGrRcL8FZLUaOp1acVeLDmTNh1HfaVCG2H0Z4StYOjn9mNpqPhdHAdjydXN4PLcSwpyUksJU_zkmYUM65yohQhQgqqqII0YbKfiFmfYs5SzlSuJCM076sSWMpyxXlKu9HJtnZpzUsLzhdz09rwsiuSPHBKOONZcPW2LmmNcxZUsbR6Ec4tCC42oIsN6OIXdAjwbWCla1j_4y6Gt5PBX_YLPmOGvQ</recordid><startdate>20220826</startdate><enddate>20220826</enddate><creator>Burra, Amarender G.</creator><creator>Uredi, Dilipkumar</creator><creator>Motati, Damoder R.</creator><creator>Fronczek, Frank R.</creator><creator>Watkins, E. Blake</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-7505-0083</orcidid></search><sort><creationdate>20220826</creationdate><title>Remote Functionalization of 8‐Substituted Quinolines with para‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes</title><author>Burra, Amarender G. ; Uredi, Dilipkumar ; Motati, Damoder R. ; Fronczek, Frank R. ; Watkins, E. Blake</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3171-cc947d363089f71ff11aca3f3fe428c52ab53098498f7fc81375fde8487f9943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>8-Aminoquinoline amide</topic><topic>Alkylation</topic><topic>Aminoquinolines</topic><topic>Copper (II)</topic><topic>Electrophilic addition</topic><topic>Organic compounds</topic><topic>Quinones</topic><topic>Substrates</topic><topic>Tri(hetero)arylmethanes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burra, Amarender G.</creatorcontrib><creatorcontrib>Uredi, Dilipkumar</creatorcontrib><creatorcontrib>Motati, Damoder R.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Watkins, E. Blake</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Burra, Amarender G.</au><au>Uredi, Dilipkumar</au><au>Motati, Damoder R.</au><au>Fronczek, Frank R.</au><au>Watkins, E. Blake</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Remote Functionalization of 8‐Substituted Quinolines with para‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes</atitle><jtitle>European journal of organic chemistry</jtitle><date>2022-08-26</date><risdate>2022</risdate><volume>2022</volume><issue>32</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A C(5)−H remote functionalization of 8‐aminoquinoline derivatives with para‐quinone methides, affording direct access to unsymmetrical tri(hetero)arylmethanes in 69–96 % yield is described. This method provides diverse tri(hetero)arylmethanes with a broad scope and in a regioselective manner. The transformation works well with electron‐rich and electron‐deficient substrates.
An expedient method for the preparation of unsymmetrical tri(hetero)arylmethanes from para‐quinone methides and derivatives of 8‐aminoquinoline under copper catalysis is described.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202200191</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7505-0083</orcidid></addata></record> |
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| language | eng |
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| source | Wiley-Blackwell Journals |
| subjects | 8-Aminoquinoline amide Alkylation Aminoquinolines Copper (II) Electrophilic addition Organic compounds Quinones Substrates Tri(hetero)arylmethanes |
| title | Remote Functionalization of 8‐Substituted Quinolines with para‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes |
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