Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in...
Gespeichert in:
| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2010/01/01, Vol.58(1), pp.23-26 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 26 |
|---|---|
| container_issue | 1 |
| container_start_page | 23 |
| container_title | Chemical & Pharmaceutical Bulletin |
| container_volume | 58 |
| creator | Nematollahi, Davood Bamzadeh, Maryam Shayani-Jam, Hasan |
| description | Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in Michael addition reaction with phenyl-Meldrum's acid to form corresponding products. We derived some new “highly oxygenated compounds with catechol ring” with good yields based on electrochemical oxidation in the controlled potential condition in aqueous solutions, without toxic reagents and solvents at carbon electrode in an undivided cell, using an environmentally friendly method. Furthermore, the observed homogeneous rate constants (kobs) of the chemical reaction between o-benzoquinone and phenyl-Meldrum's acid were estimated by comparing the experimental cyclic voltammetric curves with the digitally simulated ones. |
| doi_str_mv | 10.1248/cpb.58.23 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1460426657</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3133722281</sourcerecordid><originalsourceid>FETCH-LOGICAL-c658t-5814fe897a8aa2dc97794237e7deec570476dea30d27e4485a7d1b0de13cff5c3</originalsourceid><addsrcrecordid>eNpFkE9v1DAQxS0EokvhwBdAljhUPWQZ_4uTC1K12gKiqJWAc-S1JyQrr7O1E8R--3qbdjl45jC_eW_8CHnPYMm4rD7Z_WapqiUXL8iCCakLxbl4SRYAUBdclOKMvElpC8AVaPGanHEAqeoSFuR-7dGOcbAd7nprPL391zsz9kOgQ0tXZkTbDT7RPtCxQ3oXMWGweBzedRgOvviB3sVpd5Hole3dkv48hEymPlETHP3eBxx7S9d_jZ8edd-SV63xCd899XPy-3r9a_W1uLn98m11dVPYUlVjoSomW6xqbSpjuLO11rXkQqN2iFZpkLp0aAQ4rlHKShnt2AYcMmHbVllxTj7Ouvs43E-YxmY7TDFky4bJEiQvS6UzdTlTNg4pRWybfex3Jh4aBs0x3CaH26iq4SKzH54Up80O3Yl8TjMD1zOQp8cwh-Dz9__72qQfc84bWR1AVcByk_lxcSy6LEFpmYU-z0LbNJo_eHIyMWfp8fkmNpe8exp0JjYYxAMotaIH</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1460426657</pqid></control><display><type>article</type><title>Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Nematollahi, Davood ; Bamzadeh, Maryam ; Shayani-Jam, Hasan</creator><creatorcontrib>Nematollahi, Davood ; Bamzadeh, Maryam ; Shayani-Jam, Hasan ; Faculty of Chemistry ; Bu-Ali-Sina University</creatorcontrib><description>Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in Michael addition reaction with phenyl-Meldrum's acid to form corresponding products. We derived some new “highly oxygenated compounds with catechol ring” with good yields based on electrochemical oxidation in the controlled potential condition in aqueous solutions, without toxic reagents and solvents at carbon electrode in an undivided cell, using an environmentally friendly method. Furthermore, the observed homogeneous rate constants (kobs) of the chemical reaction between o-benzoquinone and phenyl-Meldrum's acid were estimated by comparing the experimental cyclic voltammetric curves with the digitally simulated ones.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.58.23</identifier><identifier>PMID: 20045960</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>catechol ; Catechols - chemistry ; cyclic voltammetry ; digital simulation ; Dioxanes - chemistry ; Electrochemistry ; highly oxygenated compound ; homogeneous rate constant ; Oxidation-Reduction ; phenyl-Meldrum's acid</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2010/01/01, Vol.58(1), pp.23-26</ispartof><rights>2010 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c658t-5814fe897a8aa2dc97794237e7deec570476dea30d27e4485a7d1b0de13cff5c3</citedby><cites>FETCH-LOGICAL-c658t-5814fe897a8aa2dc97794237e7deec570476dea30d27e4485a7d1b0de13cff5c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20045960$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nematollahi, Davood</creatorcontrib><creatorcontrib>Bamzadeh, Maryam</creatorcontrib><creatorcontrib>Shayani-Jam, Hasan</creatorcontrib><creatorcontrib>Faculty of Chemistry</creatorcontrib><creatorcontrib>Bu-Ali-Sina University</creatorcontrib><title>Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in Michael addition reaction with phenyl-Meldrum's acid to form corresponding products. We derived some new “highly oxygenated compounds with catechol ring” with good yields based on electrochemical oxidation in the controlled potential condition in aqueous solutions, without toxic reagents and solvents at carbon electrode in an undivided cell, using an environmentally friendly method. Furthermore, the observed homogeneous rate constants (kobs) of the chemical reaction between o-benzoquinone and phenyl-Meldrum's acid were estimated by comparing the experimental cyclic voltammetric curves with the digitally simulated ones.</description><subject>catechol</subject><subject>Catechols - chemistry</subject><subject>cyclic voltammetry</subject><subject>digital simulation</subject><subject>Dioxanes - chemistry</subject><subject>Electrochemistry</subject><subject>highly oxygenated compound</subject><subject>homogeneous rate constant</subject><subject>Oxidation-Reduction</subject><subject>phenyl-Meldrum's acid</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE9v1DAQxS0EokvhwBdAljhUPWQZ_4uTC1K12gKiqJWAc-S1JyQrr7O1E8R--3qbdjl45jC_eW_8CHnPYMm4rD7Z_WapqiUXL8iCCakLxbl4SRYAUBdclOKMvElpC8AVaPGanHEAqeoSFuR-7dGOcbAd7nprPL391zsz9kOgQ0tXZkTbDT7RPtCxQ3oXMWGweBzedRgOvviB3sVpd5Hole3dkv48hEymPlETHP3eBxx7S9d_jZ8edd-SV63xCd899XPy-3r9a_W1uLn98m11dVPYUlVjoSomW6xqbSpjuLO11rXkQqN2iFZpkLp0aAQ4rlHKShnt2AYcMmHbVllxTj7Ouvs43E-YxmY7TDFky4bJEiQvS6UzdTlTNg4pRWybfex3Jh4aBs0x3CaH26iq4SKzH54Up80O3Yl8TjMD1zOQp8cwh-Dz9__72qQfc84bWR1AVcByk_lxcSy6LEFpmYU-z0LbNJo_eHIyMWfp8fkmNpe8exp0JjYYxAMotaIH</recordid><startdate>20100101</startdate><enddate>20100101</enddate><creator>Nematollahi, Davood</creator><creator>Bamzadeh, Maryam</creator><creator>Shayani-Jam, Hasan</creator><general>The Pharmaceutical Society of Japan</general><general>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></search><sort><creationdate>20100101</creationdate><title>Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation</title><author>Nematollahi, Davood ; Bamzadeh, Maryam ; Shayani-Jam, Hasan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c658t-5814fe897a8aa2dc97794237e7deec570476dea30d27e4485a7d1b0de13cff5c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>catechol</topic><topic>Catechols - chemistry</topic><topic>cyclic voltammetry</topic><topic>digital simulation</topic><topic>Dioxanes - chemistry</topic><topic>Electrochemistry</topic><topic>highly oxygenated compound</topic><topic>homogeneous rate constant</topic><topic>Oxidation-Reduction</topic><topic>phenyl-Meldrum's acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nematollahi, Davood</creatorcontrib><creatorcontrib>Bamzadeh, Maryam</creatorcontrib><creatorcontrib>Shayani-Jam, Hasan</creatorcontrib><creatorcontrib>Faculty of Chemistry</creatorcontrib><creatorcontrib>Bu-Ali-Sina University</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><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nematollahi, Davood</au><au>Bamzadeh, Maryam</au><au>Shayani-Jam, Hasan</au><aucorp>Faculty of Chemistry</aucorp><aucorp>Bu-Ali-Sina University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2010-01-01</date><risdate>2010</risdate><volume>58</volume><issue>1</issue><spage>23</spage><epage>26</epage><pages>23-26</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in Michael addition reaction with phenyl-Meldrum's acid to form corresponding products. We derived some new “highly oxygenated compounds with catechol ring” with good yields based on electrochemical oxidation in the controlled potential condition in aqueous solutions, without toxic reagents and solvents at carbon electrode in an undivided cell, using an environmentally friendly method. Furthermore, the observed homogeneous rate constants (kobs) of the chemical reaction between o-benzoquinone and phenyl-Meldrum's acid were estimated by comparing the experimental cyclic voltammetric curves with the digitally simulated ones.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>20045960</pmid><doi>10.1248/cpb.58.23</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2010/01/01, Vol.58(1), pp.23-26 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_journals_1460426657 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | catechol Catechols - chemistry cyclic voltammetry digital simulation Dioxanes - chemistry Electrochemistry highly oxygenated compound homogeneous rate constant Oxidation-Reduction phenyl-Meldrum's acid |
| title | Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T11%3A56%3A31IST&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=Electrochemical%20Oxidation%20of%20Catechols%20in%20the%20Presence%20of%20Phenyl-Meldrum's%20Acid.%20Synthesis%20and%20Kinetic%20Evaluation&rft.jtitle=Chemical%20&%20Pharmaceutical%20Bulletin&rft.au=Nematollahi,%20Davood&rft.aucorp=Faculty%20of%20Chemistry&rft.date=2010-01-01&rft.volume=58&rft.issue=1&rft.spage=23&rft.epage=26&rft.pages=23-26&rft.issn=0009-2363&rft.eissn=1347-5223&rft_id=info:doi/10.1248/cpb.58.23&rft_dat=%3Cproquest_cross%3E3133722281%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=1460426657&rft_id=info:pmid/20045960&rfr_iscdi=true |