Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process

DC FieldValueLanguage
dc.contributor.authorDi Filippo, Mara-
dc.contributor.authorBaumann, Marcus-
dc.date.accessioned2021-11-09T16:03:37Z-
dc.date.available2021-11-09T16:03:37Z-
dc.date.copyright2020 Wileyen_US
dc.date.issued2020-10-22-
dc.identifier.citationEuropean Journal of Organic Chemistryen_US
dc.identifier.issn1434-193X-
dc.identifier.urihttp://hdl.handle.net/10197/12603-
dc.description.abstractA continuous photochemical process is presented that renders a series of quinoline products via an alkene isomerization and cyclocondensation cascade. It is demonstrated that a high-power LED lamp generates the desired targets with higher productivity and efficiency than a medium-pressure Hg-lamp. The scope of this tandem process is established and allows for the generation of various substituted quinolines in high yields and with throughputs of greater than one gram per hour. Finally, this effective flow process is coupled with a telescoped hydrogenation reaction to render a series of tetrahydroquinolines including the antimalarial natural product galipinine.en_US
dc.description.sponsorshipEuropean Commission - European Regional Development Funden_US
dc.description.sponsorshipScience Foundation Irelanden_US
dc.description.sponsorshipUniversity College Dublinen_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.rightsThis is the peer reviewed version of the following article: Di Filippo, M. and Baumann, M. (2020), Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization‚ÄźCyclization Process. Eur. J. Org. Chem., 2020: 6199-6211., which has been published in final form at https://doi.org/10.1002/ejoc.202000957. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.en_US
dc.subjectQuinolineen_US
dc.subjectTetrahydroquinolineen_US
dc.subjectFlow chemistryen_US
dc.subjectPhotochemistryen_US
dc.subjectGalipinine alkaloiden_US
dc.subjectBiologically active quinolineen_US
dc.subjectAlkaloidsen_US
dc.subjectHydrogenationen_US
dc.subjectDrugsen_US
dc.subjectMetalen_US
dc.subjectEsteren_US
dc.titleContinuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Processen_US
dc.typeJournal Articleen_US
dc.internal.authorcontactothermarcus.baumann@ucd.ieen_US
dc.statusPeer revieweden_US
dc.identifier.issue39en_US
dc.identifier.startpage6199en_US
dc.identifier.endpage6211en_US
dc.identifier.doi10.1002/ejoc.202000957-
dc.neeo.contributorDi Filippo|Mara|aut|-
dc.neeo.contributorBaumann|Marcus|aut|-
dc.date.embargo2021-02-03en_US
dc.description.admin2020-10-05 JG: PDF replaced with correct versionsen_US
dc.date.updated2020-09-21T17:51:19Z-
dc.identifier.grantid12/RC/2275_P2-
dc.rights.licensehttps://creativecommons.org/licenses/by-nc-nd/3.0/ie/en_US
item.fulltextWith Fulltext-
item.grantfulltextopen-
Appears in Collections:Chemistry Research Collection
Files in This Item:
 File SizeFormat
DownloadQuinoline EurJOC post print.pdf1.07 MBAdobe PDF
Show simple item record

Page view(s)

214
Last Week
4
Last month
28
checked on Jan 17, 2022

Download(s)

19
checked on Jan 17, 2022

Google ScholarTM

Check

Altmetric


If you are a publisher or author and have copyright concerns for any item, please email research.repository@ucd.ie and the item will be withdrawn immediately. The author or person responsible for depositing the article will be contacted within one business day.