A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreov...
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| Veröffentlicht in: | RSC advances 2019-09, Vol.9 (5), p.295-299 |
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| container_issue | 5 |
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| container_title | RSC advances |
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| creator | Gao, Yu-Qi Hou, Yi Zhu, Liming Chen, Guzhou Xu, Dongyang Zhang, Sheng-Yong He, Yupeng Xie, Weiqing |
| description | A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid
via
counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed
via
tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is
in situ
captured by nucleophiles to afford hybrid flavonoids.
An efficient protocol for the synthesis of hybrid flavonoids was achieved
via
a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles. |
| doi_str_mv | 10.1039/c9ra07198a |
| format | Article |
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via
counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed
via
tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is
in situ
captured by nucleophiles to afford hybrid flavonoids.
An efficient protocol for the synthesis of hybrid flavonoids was achieved
via
a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c9ra07198a</identifier><identifier>PMID: 35528404</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Catalysis ; Chemistry ; Dehydration ; Flavonoids ; Isomerization ; Nucleophiles ; Phosphoric acid ; Synthesis</subject><ispartof>RSC advances, 2019-09, Vol.9 (5), p.295-299</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-bb5b4d03b9b9f1fcbdf1b5dac078fa7a7deb2cf9ad332b973a44947c50916bcb3</citedby><cites>FETCH-LOGICAL-c428t-bb5b4d03b9b9f1fcbdf1b5dac078fa7a7deb2cf9ad332b973a44947c50916bcb3</cites><orcidid>0000-0002-8343-2364</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071822/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071822/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35528404$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gao, Yu-Qi</creatorcontrib><creatorcontrib>Hou, Yi</creatorcontrib><creatorcontrib>Zhu, Liming</creatorcontrib><creatorcontrib>Chen, Guzhou</creatorcontrib><creatorcontrib>Xu, Dongyang</creatorcontrib><creatorcontrib>Zhang, Sheng-Yong</creatorcontrib><creatorcontrib>He, Yupeng</creatorcontrib><creatorcontrib>Xie, Weiqing</creatorcontrib><title>A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid
via
counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed
via
tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is
in situ
captured by nucleophiles to afford hybrid flavonoids.
An efficient protocol for the synthesis of hybrid flavonoids was achieved
via
a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Dehydration</subject><subject>Flavonoids</subject><subject>Isomerization</subject><subject>Nucleophiles</subject><subject>Phosphoric acid</subject><subject>Synthesis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkc1LHEEQxRtRVHQv3iMNuYTAmP6ame5LYFliEhCEkNyEpj93Wma71-7ZxfnvM7pmo9alCt6PR1U9AC4wusKIii9GZIVaLLg6AKcEsaYiqBGHr-YTMCvlHk3V1Jg0-Bic0LomnCF2Cu7mUIdUhVjWITsLyxiHzpVQYPKwG3UOFvpebVNMwRboc1pBUnWjzelxNJ3qTYoO2hy2LkI9wm0oQfcO9mHZDefgyKu-uNlLPwN_rr_9Xvyobm6__1zMbyrDCB8qrWvNLKJaaOGxN9p6rGurDGq5V61qrdPEeKEspUSLlirGBGtNjQRutNH0DHzd-a43euWscXHIqpfrHFYqjzKpIN8qMXRymbZSTJ_jhEwGn14McnrYuDLIVSjG9b2KLm2KJE2DGa8Fbyb04zv0Pm1ynM6ThAiCOKeknqjPO8rkVEp2fr8MRvIpN7kQv-bPuc0n-PL1-nv0X0oT8GEH5GL26v_g6V-eX589</recordid><startdate>20190916</startdate><enddate>20190916</enddate><creator>Gao, Yu-Qi</creator><creator>Hou, Yi</creator><creator>Zhu, Liming</creator><creator>Chen, Guzhou</creator><creator>Xu, Dongyang</creator><creator>Zhang, Sheng-Yong</creator><creator>He, Yupeng</creator><creator>Xie, Weiqing</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-8343-2364</orcidid></search><sort><creationdate>20190916</creationdate><title>A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light</title><author>Gao, Yu-Qi ; Hou, Yi ; Zhu, Liming ; Chen, Guzhou ; Xu, Dongyang ; Zhang, Sheng-Yong ; He, Yupeng ; Xie, Weiqing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-bb5b4d03b9b9f1fcbdf1b5dac078fa7a7deb2cf9ad332b973a44947c50916bcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Dehydration</topic><topic>Flavonoids</topic><topic>Isomerization</topic><topic>Nucleophiles</topic><topic>Phosphoric acid</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gao, Yu-Qi</creatorcontrib><creatorcontrib>Hou, Yi</creatorcontrib><creatorcontrib>Zhu, Liming</creatorcontrib><creatorcontrib>Chen, Guzhou</creatorcontrib><creatorcontrib>Xu, Dongyang</creatorcontrib><creatorcontrib>Zhang, Sheng-Yong</creatorcontrib><creatorcontrib>He, Yupeng</creatorcontrib><creatorcontrib>Xie, Weiqing</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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gao, Yu-Qi</au><au>Hou, Yi</au><au>Zhu, Liming</au><au>Chen, Guzhou</au><au>Xu, Dongyang</au><au>Zhang, Sheng-Yong</au><au>He, Yupeng</au><au>Xie, Weiqing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2019-09-16</date><risdate>2019</risdate><volume>9</volume><issue>5</issue><spage>295</spage><epage>299</epage><pages>295-299</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A bio-inspired synthesis of hybrid flavonoids from 2-hydroxylchalcone is described. Under the irradiation of 24 W CFL, 2-hydroxychalcone reacts with various nucleophiles to deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid
via
counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed
via
tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone to form a transient flavylium cation, which is
in situ
captured by nucleophiles to afford hybrid flavonoids.
An efficient protocol for the synthesis of hybrid flavonoids was achieved
via
a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35528404</pmid><doi>10.1039/c9ra07198a</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8343-2364</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Catalysis Chemistry Dehydration Flavonoids Isomerization Nucleophiles Phosphoric acid Synthesis |
| title | A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light |
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