Chemo‐ and Regioselective Construction of Functionalized Isocoumarin, Flavone, and Isoquinolinedione via a One‐pot Reaction of o‐Quinol Acetate and Soft Nucleophiles
A one‐pot strategy for the synthesis of substituted isocoumarin, flavone, and isoquinolinedione derivatives through a switchable C‐arylation/lactonization or SNAr reaction from a wide range of soft nucleophiles and o‐quinol acetates has been developed. This base‐mediated protocol proceeds under tran...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2023-09, Vol.365 (17), p.2900-2911 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Jang, Yeong‐Jiunn Chen, Guan‐Yu Jhan, Yun‐Lian Lo, Pei‐Ting Hsu, Wei‐Yu Wang, Ke Hsu, Ya‐Ting Lee, Chia‐Lin Yang, Yu‐Liang Wu, Yang‐Chang |
| description | A one‐pot strategy for the synthesis of substituted isocoumarin, flavone, and isoquinolinedione derivatives through a switchable C‐arylation/lactonization or SNAr reaction from a wide range of soft nucleophiles and o‐quinol acetates has been developed. This base‐mediated protocol proceeds under transition‐metal‐free conditions and selectively affords various heteroarenes in 13–98% yields from readily prepared or commercially available 1,3‐dicarbonyl and α‐EWG‐substituted carbonyl compounds. The synthetic utility is further demonstrated in the synthesis of potential anti‐HIV and anti‐coronavirus derivatives and COX‐2 inhibitors. In addition, detailed experimental and computational studies are performed to provide an intensive understanding and strong support of the reaction mechanism. |
| doi_str_mv | 10.1002/adsc.202201291 |
| format | Article |
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This base‐mediated protocol proceeds under transition‐metal‐free conditions and selectively affords various heteroarenes in 13–98% yields from readily prepared or commercially available 1,3‐dicarbonyl and α‐EWG‐substituted carbonyl compounds. The synthetic utility is further demonstrated in the synthesis of potential anti‐HIV and anti‐coronavirus derivatives and COX‐2 inhibitors. In addition, detailed experimental and computational studies are performed to provide an intensive understanding and strong support of the reaction mechanism.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202201291</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Acetates ; Carbonyl compounds ; Carbonyls ; Chemoselectivity ; Computational chemistry ; COX-2 inhibitors ; Inflammation ; Nucleophiles ; Quinones ; Reaction mechanisms ; Regioselectivity ; Substitutes ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2023-09, Vol.365 (17), p.2900-2911</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3171-22f4d7308f05d29186e709ba8b55c130904d58e05230d771e5b72f6458c4e2eb3</citedby><cites>FETCH-LOGICAL-c3171-22f4d7308f05d29186e709ba8b55c130904d58e05230d771e5b72f6458c4e2eb3</cites><orcidid>0000-0001-8637-924X</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%2Fadsc.202201291$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202201291$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27933,27934,45583,45584</link.rule.ids></links><search><creatorcontrib>Jang, Yeong‐Jiunn</creatorcontrib><creatorcontrib>Chen, Guan‐Yu</creatorcontrib><creatorcontrib>Jhan, Yun‐Lian</creatorcontrib><creatorcontrib>Lo, Pei‐Ting</creatorcontrib><creatorcontrib>Hsu, Wei‐Yu</creatorcontrib><creatorcontrib>Wang, Ke</creatorcontrib><creatorcontrib>Hsu, Ya‐Ting</creatorcontrib><creatorcontrib>Lee, Chia‐Lin</creatorcontrib><creatorcontrib>Yang, Yu‐Liang</creatorcontrib><creatorcontrib>Wu, Yang‐Chang</creatorcontrib><title>Chemo‐ and Regioselective Construction of Functionalized Isocoumarin, Flavone, and Isoquinolinedione via a One‐pot Reaction of o‐Quinol Acetate and Soft Nucleophiles</title><title>Advanced synthesis & catalysis</title><description>A one‐pot strategy for the synthesis of substituted isocoumarin, flavone, and isoquinolinedione derivatives through a switchable C‐arylation/lactonization or SNAr reaction from a wide range of soft nucleophiles and o‐quinol acetates has been developed. This base‐mediated protocol proceeds under transition‐metal‐free conditions and selectively affords various heteroarenes in 13–98% yields from readily prepared or commercially available 1,3‐dicarbonyl and α‐EWG‐substituted carbonyl compounds. The synthetic utility is further demonstrated in the synthesis of potential anti‐HIV and anti‐coronavirus derivatives and COX‐2 inhibitors. 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| subjects | Acetates Carbonyl compounds Carbonyls Chemoselectivity Computational chemistry COX-2 inhibitors Inflammation Nucleophiles Quinones Reaction mechanisms Regioselectivity Substitutes Synthesis |
| title | Chemo‐ and Regioselective Construction of Functionalized Isocoumarin, Flavone, and Isoquinolinedione via a One‐pot Reaction of o‐Quinol Acetate and Soft Nucleophiles |
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