Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans
Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are f...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2024/06/19, Vol.72(6), pp.566-569 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 569 |
|---|---|
| container_issue | 6 |
| container_start_page | 566 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 72 |
| creator | Sawama, Yoshinari Nakajima, Keiichiro Aijima, Takaaki Mae, Miyu Komagawa, Shinsuke Nakata, Hiroki Sajiki, Hironao Akai, Shuji |
| description | Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative coupling of hydroquinones bearing an electron-withdrawing group at the C2 position with olefins to dihydrobenzofurans in the presence of the Lewis acidic FeCl3 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidant. Furthermore, this method was applied to the oxidative coupling of N-electron-withdrawing group-substituted 4-aminophenol. |
| doi_str_mv | 10.1248/cpb.c24-00231 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3070824549</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3080054157</sourcerecordid><originalsourceid>FETCH-LOGICAL-c401t-25a7b8f85e4a6c904af9b24cedc6f8f71363006bbee01c645a2363cc95dab32f3</originalsourceid><addsrcrecordid>eNpd0M1rFDEYBvBQLO22evQqA168TPvmaz6OslUrFJaCnkMm86abZTZZk5lq_evN7LYr9JIc8uPhyUPIewpXlInm2uy6K8NECcA4PSELykVdSsb4G7IAgLZkvOLn5CKlTSYSan5GznnTtHUrxYLcr_64Xo_uEYtlmHaD8w9FsMXtUx_Dr8n54LG4wege9yYVv924LlYDWudTMYbixq1n2qH_G-wUtU9vyanVQ8J3z_cl-fn1y4_lbXm3-vZ9-fmuNALoWDKp666xjUShK9OC0LbtmDDYm8o2tqa5NkDVdYhATSWknj9iTCt73XFm-SX5dMjdzU0xjWrrksFh0B7DlBSHGhompGgz_fiKbsIUfW6XVQMgBZV1VuVBmRhSimjVLrqtjk-Kgpq3VnlrlbdW-62z__CcOnVb7I_6ZdwMlgewSaN-wCPQcXRmwH1czVQ1H8fY_69rHRV6_g83w5Lf</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3080054157</pqid></control><display><type>article</type><title>Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans</title><source>J-STAGE Free</source><source>MEDLINE</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Sawama, Yoshinari ; Nakajima, Keiichiro ; Aijima, Takaaki ; Mae, Miyu ; Komagawa, Shinsuke ; Nakata, Hiroki ; Sajiki, Hironao ; Akai, Shuji</creator><creatorcontrib>Sawama, Yoshinari ; Nakajima, Keiichiro ; Aijima, Takaaki ; Mae, Miyu ; Komagawa, Shinsuke ; Nakata, Hiroki ; Sajiki, Hironao ; Akai, Shuji</creatorcontrib><description>Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative coupling of hydroquinones bearing an electron-withdrawing group at the C2 position with olefins to dihydrobenzofurans in the presence of the Lewis acidic FeCl3 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidant. Furthermore, this method was applied to the oxidative coupling of N-electron-withdrawing group-substituted 4-aminophenol.</description><identifier>ISSN: 0009-2363</identifier><identifier>ISSN: 1347-5223</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c24-00231</identifier><identifier>PMID: 38897954</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Acidic oxides ; Alkenes ; Alkenes - chemistry ; Aminophenol ; Benzofurans - chemical synthesis ; Benzofurans - chemistry ; Benzoquinone ; Benzoquinones - chemical synthesis ; Benzoquinones - chemistry ; Bioactive compounds ; Chlorides - chemistry ; Ferric chloride ; Ferric Compounds - chemistry ; heterocycle ; Hydroquinone ; Hydroquinones - chemical synthesis ; Hydroquinones - chemistry ; Molecular Structure ; Natural products ; Oxidants ; Oxidation ; Oxidation-Reduction ; Oxidative Coupling ; oxidative functionalization ; Oxidizing agents ; p-Aminophenol ; Substitutes</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2024/06/19, Vol.72(6), pp.566-569</ispartof><rights>2024 Author(s) This is an open access article distributed under the terms of Creative Commons Attribution 4.0 License (https://creativecommons.org/licenses/by-nc/4.0/). Published by The Pharmaceutical Society of Japan</rights><rights>2024. This work is published under https://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c401t-25a7b8f85e4a6c904af9b24cedc6f8f71363006bbee01c645a2363cc95dab32f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38897954$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sawama, Yoshinari</creatorcontrib><creatorcontrib>Nakajima, Keiichiro</creatorcontrib><creatorcontrib>Aijima, Takaaki</creatorcontrib><creatorcontrib>Mae, Miyu</creatorcontrib><creatorcontrib>Komagawa, Shinsuke</creatorcontrib><creatorcontrib>Nakata, Hiroki</creatorcontrib><creatorcontrib>Sajiki, Hironao</creatorcontrib><creatorcontrib>Akai, Shuji</creatorcontrib><title>Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative coupling of hydroquinones bearing an electron-withdrawing group at the C2 position with olefins to dihydrobenzofurans in the presence of the Lewis acidic FeCl3 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidant. Furthermore, this method was applied to the oxidative coupling of N-electron-withdrawing group-substituted 4-aminophenol.</description><subject>Acidic oxides</subject><subject>Alkenes</subject><subject>Alkenes - chemistry</subject><subject>Aminophenol</subject><subject>Benzofurans - chemical synthesis</subject><subject>Benzofurans - chemistry</subject><subject>Benzoquinone</subject><subject>Benzoquinones - chemical synthesis</subject><subject>Benzoquinones - chemistry</subject><subject>Bioactive compounds</subject><subject>Chlorides - chemistry</subject><subject>Ferric chloride</subject><subject>Ferric Compounds - chemistry</subject><subject>heterocycle</subject><subject>Hydroquinone</subject><subject>Hydroquinones - chemical synthesis</subject><subject>Hydroquinones - chemistry</subject><subject>Molecular Structure</subject><subject>Natural products</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Oxidative Coupling</subject><subject>oxidative functionalization</subject><subject>Oxidizing agents</subject><subject>p-Aminophenol</subject><subject>Substitutes</subject><issn>0009-2363</issn><issn>1347-5223</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0M1rFDEYBvBQLO22evQqA168TPvmaz6OslUrFJaCnkMm86abZTZZk5lq_evN7LYr9JIc8uPhyUPIewpXlInm2uy6K8NECcA4PSELykVdSsb4G7IAgLZkvOLn5CKlTSYSan5GznnTtHUrxYLcr_64Xo_uEYtlmHaD8w9FsMXtUx_Dr8n54LG4wege9yYVv924LlYDWudTMYbixq1n2qH_G-wUtU9vyanVQ8J3z_cl-fn1y4_lbXm3-vZ9-fmuNALoWDKp666xjUShK9OC0LbtmDDYm8o2tqa5NkDVdYhATSWknj9iTCt73XFm-SX5dMjdzU0xjWrrksFh0B7DlBSHGhompGgz_fiKbsIUfW6XVQMgBZV1VuVBmRhSimjVLrqtjk-Kgpq3VnlrlbdW-62z__CcOnVb7I_6ZdwMlgewSaN-wCPQcXRmwH1czVQ1H8fY_69rHRV6_g83w5Lf</recordid><startdate>20240619</startdate><enddate>20240619</enddate><creator>Sawama, Yoshinari</creator><creator>Nakajima, Keiichiro</creator><creator>Aijima, Takaaki</creator><creator>Mae, Miyu</creator><creator>Komagawa, Shinsuke</creator><creator>Nakata, Hiroki</creator><creator>Sajiki, Hironao</creator><creator>Akai, Shuji</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20240619</creationdate><title>Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans</title><author>Sawama, Yoshinari ; Nakajima, Keiichiro ; Aijima, Takaaki ; Mae, Miyu ; Komagawa, Shinsuke ; Nakata, Hiroki ; Sajiki, Hironao ; Akai, Shuji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c401t-25a7b8f85e4a6c904af9b24cedc6f8f71363006bbee01c645a2363cc95dab32f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acidic oxides</topic><topic>Alkenes</topic><topic>Alkenes - chemistry</topic><topic>Aminophenol</topic><topic>Benzofurans - chemical synthesis</topic><topic>Benzofurans - chemistry</topic><topic>Benzoquinone</topic><topic>Benzoquinones - chemical synthesis</topic><topic>Benzoquinones - chemistry</topic><topic>Bioactive compounds</topic><topic>Chlorides - chemistry</topic><topic>Ferric chloride</topic><topic>Ferric Compounds - chemistry</topic><topic>heterocycle</topic><topic>Hydroquinone</topic><topic>Hydroquinones - chemical synthesis</topic><topic>Hydroquinones - chemistry</topic><topic>Molecular Structure</topic><topic>Natural products</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Oxidative Coupling</topic><topic>oxidative functionalization</topic><topic>Oxidizing agents</topic><topic>p-Aminophenol</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawama, Yoshinari</creatorcontrib><creatorcontrib>Nakajima, Keiichiro</creatorcontrib><creatorcontrib>Aijima, Takaaki</creatorcontrib><creatorcontrib>Mae, Miyu</creatorcontrib><creatorcontrib>Komagawa, Shinsuke</creatorcontrib><creatorcontrib>Nakata, Hiroki</creatorcontrib><creatorcontrib>Sajiki, Hironao</creatorcontrib><creatorcontrib>Akai, Shuji</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sawama, Yoshinari</au><au>Nakajima, Keiichiro</au><au>Aijima, Takaaki</au><au>Mae, Miyu</au><au>Komagawa, Shinsuke</au><au>Nakata, Hiroki</au><au>Sajiki, Hironao</au><au>Akai, Shuji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2024-06-19</date><risdate>2024</risdate><volume>72</volume><issue>6</issue><spage>566</spage><epage>569</epage><pages>566-569</pages><artnum>c24-00231</artnum><issn>0009-2363</issn><issn>1347-5223</issn><eissn>1347-5223</eissn><abstract>Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative coupling of hydroquinones bearing an electron-withdrawing group at the C2 position with olefins to dihydrobenzofurans in the presence of the Lewis acidic FeCl3 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidant. Furthermore, this method was applied to the oxidative coupling of N-electron-withdrawing group-substituted 4-aminophenol.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>38897954</pmid><doi>10.1248/cpb.c24-00231</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2024/06/19, Vol.72(6), pp.566-569 |
| issn | 0009-2363 1347-5223 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3070824549 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Acidic oxides Alkenes Alkenes - chemistry Aminophenol Benzofurans - chemical synthesis Benzofurans - chemistry Benzoquinone Benzoquinones - chemical synthesis Benzoquinones - chemistry Bioactive compounds Chlorides - chemistry Ferric chloride Ferric Compounds - chemistry heterocycle Hydroquinone Hydroquinones - chemical synthesis Hydroquinones - chemistry Molecular Structure Natural products Oxidants Oxidation Oxidation-Reduction Oxidative Coupling oxidative functionalization Oxidizing agents p-Aminophenol Substitutes |
| title | Oxidative Coupling of Hydroquinone Derivatives with Olefins to Dihydrobenzofurans |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T22%3A33%3A12IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Oxidative%20Coupling%20of%20Hydroquinone%20Derivatives%20with%20Olefins%20to%20Dihydrobenzofurans&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=Sawama,%20Yoshinari&rft.date=2024-06-19&rft.volume=72&rft.issue=6&rft.spage=566&rft.epage=569&rft.pages=566-569&rft.artnum=c24-00231&rft.issn=0009-2363&rft.eissn=1347-5223&rft_id=info:doi/10.1248/cpb.c24-00231&rft_dat=%3Cproquest_cross%3E3080054157%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3080054157&rft_id=info:pmid/38897954&rfr_iscdi=true |