Synthesis and reactivity of dihalofuranones

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dc.check.date2023-08-01
dc.check.infoAccess to this article is restricted until 12 months after publication by request of the publisher.en
dc.contributor.authorLyons, Thérèse A.
dc.contributor.authorGahan, Cormac G. M.
dc.contributor.authorO'Sullivan, Timothy P.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2022-12-15T13:41:11Z
dc.date.available2022-12-15T13:41:11Z
dc.date.issued2022-08-01
dc.date.updated2022-12-12T14:58:14Z
dc.description.abstractHalogenated furanones have been found to act as potent quorum sensing inhibitors in several bacterial species. It is believed that dihalofuranones covalently bind to the LuxS enzyme, which is necessary for autoinducer-2 synthesis. In addition to their antimicrobial activity, halogen-ated furanones also possess anti-cancer, antioxidant, and depigmentation properties. However, traditional routes to these compounds are low-yielding and capricious. The aim of this study was to investigate higher-yielding preparations of gem-dihalofuranones and compare their reactivity using Suzuki chemistry. Ramirez dibromoolefination of maleic anhydride was optimised using a variety of conditions. A similar route was investigated for the preparation of bromofluorofuranones and dichlorofuranones. The conversion of a dichlorofuranone to the corresponding iodofuranone derivatives using microwave-assisted Finkelstein chemistry was also studied. Lastly, the reactivity of the different dihalofuranones was compared by Pd-mediated coupling with phenylboronic acid. A higher-yielding, concise synthesis of dibromofuranones was developed using a modified Ramirez reaction. Additionally, a telescoped preparation of dichlorofuranone was higher yielding than previous approaches. Bromine-and iodine-substituted dihalofuranones proved more reactive than their chlorine-substituted analogues. Higher yielding routes to bromine-, fluorine-, chlorine-and iodine-containing dihalofuranones were successfully developed. Suzuki couplings of gem-dihalofuranones were found to proceed with high stereoselectivity.en
dc.description.sponsorshipScience Foundation Ireland (SFI/12/RC/2273)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationLyons T. A., Gahan C. G. M. and O'Sullivan T. P. (2022) 'Synthesis and reactivity of dihalofuranones', Letters in Organic Chemistry, 19(8), pp. 662-667. doi: 10.2174/1570178618666211027103633en
dc.identifier.doi10.2174/1570178618666211027103633en
dc.identifier.eissn1875-6255
dc.identifier.endpage667en
dc.identifier.issn1570-1786
dc.identifier.issued8en
dc.identifier.journaltitleLetters in Organic Chemistryen
dc.identifier.startpage662en
dc.identifier.urihttp://hdl.handle.net/10468/13969
dc.identifier.volume19en
dc.internal.IRISemailaddresstim.osullivan@ucc.ieen
dc.internal.authorcontactotherTim O'Sullivan, Pharmacy, University College Cork, Cork, Ireland. +353-21-490-3000 Email: tim.osullivan@ucc.ieen
dc.internal.availabilityFull text availableen
dc.internal.copyrightcheckedNo
dc.internal.emailaddresse.noonan@ucc.ieen
dc.internal.licenseacceptanceYesen
dc.internal.rssid626185493
dc.language.isoenen
dc.publisherBentham Science Publishersen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2273/IE/Alimentary Pharmabiotic Centre (APC) - Interfacing Food & Medicine/en
dc.rights© 2022, Bentham Science Publishers. This is the accepted version of the following item: Lyons T. A., Gahan C. G. M. and O'Sullivan T. P. (2022) 'Synthesis and reactivity of dihalofuranones', Letters in Organic Chemistry, 19(8), pp. 662-667, doi: 10.2174/1570178618666211027103633. The published manuscript is available at EurekaSelect via http://www.eurekaselect.com/10.2174/1570178618666211027103633en
dc.subjectQuorum sensingen
dc.subjectSuzuki couplingen
dc.subjectAutoinducersen
dc.subjectDihalofuranonesen
dc.subjectHeterocyclesen
dc.subjectResistanceen
dc.titleSynthesis and reactivity of dihalofuranonesen
dc.typeArticle (peer-reviewed)en
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