Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine
A concise, novel and flexible metal‐free single step to synthesize functionalized quinolines is reported. Triflic anhydride‐mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio‐ and chemosel...
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| Veröffentlicht in: | Chemistry : a European journal 2017-11, Vol.23 (61), p.15300-15304 |
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| container_issue | 61 |
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| container_title | Chemistry : a European journal |
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| creator | Li, Lian‐Hua Niu, Zhi‐Jie Liang, Yong‐Min |
| description | A concise, novel and flexible metal‐free single step to synthesize functionalized quinolines is reported. Triflic anhydride‐mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio‐ and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.
Various functionalized quinolines are readily obtained through a metal‐free novel process. The method offers a straightforward and efficient way to construct azaheterocycle structures with excellent productivity, high regio‐ and chemoselectivity. |
| doi_str_mv | 10.1002/chem.201703832 |
| format | Article |
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Various functionalized quinolines are readily obtained through a metal‐free novel process. The method offers a straightforward and efficient way to construct azaheterocycle structures with excellent productivity, high regio‐ and chemoselectivity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201703832</identifier><identifier>PMID: 28885756</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Amides ; Chemical synthesis ; Chemistry ; metal-free ; Organic compounds ; Pyridines ; quinoline ; Quinolines ; regioselectivity ; Substrates ; synthesis ; triflic anhydride</subject><ispartof>Chemistry : a European journal, 2017-11, Vol.23 (61), p.15300-15304</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-1bf059bddd375f68e9d49bf0ea61cc12a87bde25ea9145bd05afb0274aafbb443</citedby><cites>FETCH-LOGICAL-c4102-1bf059bddd375f68e9d49bf0ea61cc12a87bde25ea9145bd05afb0274aafbb443</cites><orcidid>0000-0002-6167-6536</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%2Fchem.201703832$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201703832$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28885756$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Lian‐Hua</creatorcontrib><creatorcontrib>Niu, Zhi‐Jie</creatorcontrib><creatorcontrib>Liang, Yong‐Min</creatorcontrib><title>Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A concise, novel and flexible metal‐free single step to synthesize functionalized quinolines is reported. Triflic anhydride‐mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio‐ and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.
Various functionalized quinolines are readily obtained through a metal‐free novel process. The method offers a straightforward and efficient way to construct azaheterocycle structures with excellent productivity, high regio‐ and chemoselectivity.</description><subject>Alkynes</subject><subject>Amides</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>metal-free</subject><subject>Organic compounds</subject><subject>Pyridines</subject><subject>quinoline</subject><subject>Quinolines</subject><subject>regioselectivity</subject><subject>Substrates</subject><subject>synthesis</subject><subject>triflic anhydride</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqF0UtPhDAUBeDGaHQc3bo0Tdy4YWwLBbokE1-JxvealLZIR6BjCxr89RZn1MSNq5vcfvcsegA4wGiGESInolLNjCCcoDANyQaYYEpwECYx3QQTxKIkiGnIdsCucwuEEIvDcBvskDRNaULjCXh7GNquUk47aEp41rei06bltf5QEt71ujW1bpWDXWVN_1xBDu8V_zKjzxot_SNvJczql2GEt9Y0pvPHxQAfrS5rLWDWVoO0np7cDn74wD2wVfLaqf31nIKns9PH-UVwdXN-Oc-uAhFhRAJclIiyQkoZJrSMU8VkxPxO8RgLgQlPk0IqQhVnOKKFRJSXBSJJxP0soiicguNV7tKa1165Lm-0E6queatM73LMfDBmNMWeHv2hC9Nb_xWjomlMogQRr2YrJaxxzqoyX1rdcDvkGOVjI_nYSP7TiD84XMf2RaPkD_-uwAO2Au-6VsM_cfn84vT6N_wTxqyZtQ</recordid><startdate>20171102</startdate><enddate>20171102</enddate><creator>Li, Lian‐Hua</creator><creator>Niu, Zhi‐Jie</creator><creator>Liang, Yong‐Min</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6167-6536</orcidid></search><sort><creationdate>20171102</creationdate><title>Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine</title><author>Li, Lian‐Hua ; Niu, Zhi‐Jie ; Liang, Yong‐Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-1bf059bddd375f68e9d49bf0ea61cc12a87bde25ea9145bd05afb0274aafbb443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Amides</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>metal-free</topic><topic>Organic compounds</topic><topic>Pyridines</topic><topic>quinoline</topic><topic>Quinolines</topic><topic>regioselectivity</topic><topic>Substrates</topic><topic>synthesis</topic><topic>triflic anhydride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Lian‐Hua</creatorcontrib><creatorcontrib>Niu, Zhi‐Jie</creatorcontrib><creatorcontrib>Liang, Yong‐Min</creatorcontrib><collection>PubMed</collection><collection>CrossRef</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>Li, Lian‐Hua</au><au>Niu, Zhi‐Jie</au><au>Liang, Yong‐Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-11-02</date><risdate>2017</risdate><volume>23</volume><issue>61</issue><spage>15300</spage><epage>15304</epage><pages>15300-15304</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A concise, novel and flexible metal‐free single step to synthesize functionalized quinolines is reported. Triflic anhydride‐mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio‐ and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.
Various functionalized quinolines are readily obtained through a metal‐free novel process. The method offers a straightforward and efficient way to construct azaheterocycle structures with excellent productivity, high regio‐ and chemoselectivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28885756</pmid><doi>10.1002/chem.201703832</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-6167-6536</orcidid></addata></record> |
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| ispartof | Chemistry : a European journal, 2017-11, Vol.23 (61), p.15300-15304 |
| issn | 0947-6539 1521-3765 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes Amides Chemical synthesis Chemistry metal-free Organic compounds Pyridines quinoline Quinolines regioselectivity Substrates synthesis triflic anhydride |
| title | Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine |
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