DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives
A switchable cascade cyclization reaction of ortho -alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of in situ generated ortho -alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2024-05, Vol.11 (10), p.2845-2850 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Xu, Shiyu Sun, Zhihui Liu, Pengyutian Wei, Yuanlin Sun, Fan Zhao, Man Wang, Ying Zhang, Ming Li, Guofeng Liang, Hong |
| description | A switchable cascade cyclization reaction of
ortho
-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of
in situ
generated
ortho
-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent regioselectivities. This transformation is metal-free, and has mild reaction conditions, high atom utilization and strong substrate applicability. |
| doi_str_mv | 10.1039/D4QO00012A |
| format | Article |
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ortho
-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of
in situ
generated
ortho
-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent regioselectivities. This transformation is metal-free, and has mild reaction conditions, high atom utilization and strong substrate applicability.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D4QO00012A</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Amines ; Catalysis ; Chemical synthesis ; Cyclic compounds ; Substitution reactions ; Substrates</subject><ispartof>Organic Chemistry Frontiers, 2024-05, Vol.11 (10), p.2845-2850</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c240t-9a74ecf36fe5fb433f4106da6a73fb3b8061f0d5ff10b45a5f87dfdefc6cbe463</cites><orcidid>0000-0002-7528-2036 ; 0000-0002-3489-0633</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Xu, Shiyu</creatorcontrib><creatorcontrib>Sun, Zhihui</creatorcontrib><creatorcontrib>Liu, Pengyutian</creatorcontrib><creatorcontrib>Wei, Yuanlin</creatorcontrib><creatorcontrib>Sun, Fan</creatorcontrib><creatorcontrib>Zhao, Man</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Zhang, Ming</creatorcontrib><creatorcontrib>Li, Guofeng</creatorcontrib><creatorcontrib>Liang, Hong</creatorcontrib><title>DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives</title><title>Organic Chemistry Frontiers</title><description>A switchable cascade cyclization reaction of
ortho
-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of
in situ
generated
ortho
-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent regioselectivities. This transformation is metal-free, and has mild reaction conditions, high atom utilization and strong substrate applicability.</description><subject>Amines</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Cyclic compounds</subject><subject>Substitution reactions</subject><subject>Substrates</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpNkF1LwzAUhoMoOOZu_AUF74TOkyZp18u5-QXCENyVSEmaZM3okpmkw_rr3ZygV-flvA_nwIPQJYYxBlLezOnLAgBwNj1BgwxYllKclaf_8jkahbD-YVgOrBigZn67TGseedt_KZmEToRoYheNs2ntbPSubQ_73sZGBRMSpxP3yd_ImIzxeyK8kat9741dJdzKxPJtE5u-5RtjVSKVNzsezU6FC3SmeRvU6HcO0fL-7nX2mD4vHp5m0-e0zijEtOQFVbUmuVZMC0qIphhyyXNeEC2ImECONUimNQZBGWd6Ukgtla7zWiiakyG6Ot7devfRqRCrteu83b-sCDBKoYQJ2VPXR6r2LgSvdLX1ZsN9X2GoDjKrP5nkGximaG4</recordid><startdate>20240514</startdate><enddate>20240514</enddate><creator>Xu, Shiyu</creator><creator>Sun, Zhihui</creator><creator>Liu, Pengyutian</creator><creator>Wei, Yuanlin</creator><creator>Sun, Fan</creator><creator>Zhao, Man</creator><creator>Wang, Ying</creator><creator>Zhang, Ming</creator><creator>Li, Guofeng</creator><creator>Liang, Hong</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-7528-2036</orcidid><orcidid>https://orcid.org/0000-0002-3489-0633</orcidid></search><sort><creationdate>20240514</creationdate><title>DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives</title><author>Xu, Shiyu ; Sun, Zhihui ; Liu, Pengyutian ; Wei, Yuanlin ; Sun, Fan ; Zhao, Man ; Wang, Ying ; Zhang, Ming ; Li, Guofeng ; Liang, Hong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c240t-9a74ecf36fe5fb433f4106da6a73fb3b8061f0d5ff10b45a5f87dfdefc6cbe463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amines</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Cyclic compounds</topic><topic>Substitution reactions</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Shiyu</creatorcontrib><creatorcontrib>Sun, Zhihui</creatorcontrib><creatorcontrib>Liu, Pengyutian</creatorcontrib><creatorcontrib>Wei, Yuanlin</creatorcontrib><creatorcontrib>Sun, Fan</creatorcontrib><creatorcontrib>Zhao, Man</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Zhang, Ming</creatorcontrib><creatorcontrib>Li, Guofeng</creatorcontrib><creatorcontrib>Liang, Hong</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Shiyu</au><au>Sun, Zhihui</au><au>Liu, Pengyutian</au><au>Wei, Yuanlin</au><au>Sun, Fan</au><au>Zhao, Man</au><au>Wang, Ying</au><au>Zhang, Ming</au><au>Li, Guofeng</au><au>Liang, Hong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2024-05-14</date><risdate>2024</risdate><volume>11</volume><issue>10</issue><spage>2845</spage><epage>2850</epage><pages>2845-2850</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A switchable cascade cyclization reaction of
ortho
-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of
in situ
generated
ortho
-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent regioselectivities. This transformation is metal-free, and has mild reaction conditions, high atom utilization and strong substrate applicability.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D4QO00012A</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7528-2036</orcidid><orcidid>https://orcid.org/0000-0002-3489-0633</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2024-05, Vol.11 (10), p.2845-2850 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_3054409083 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Amines Catalysis Chemical synthesis Cyclic compounds Substitution reactions Substrates |
| title | DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives |
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