Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process
|Title:||Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process||Authors:||Di Filippo, Mara; Baumann, Marcus||Permanent link:||http://hdl.handle.net/10197/12603||Date:||22-Oct-2020||Online since:||2021-11-09T16:03:37Z||Abstract:||A 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.||Funding Details:||European Commission - European Regional Development Fund
Science Foundation Ireland
University College Dublin
|Type of material:||Journal Article||Publisher:||Wiley||Journal:||European Journal of Organic Chemistry||Issue:||39||Start page:||6199||End page:||6211||Copyright (published version):||2020 Wiley||Keywords:||Quinoline; Tetrahydroquinoline; Flow chemistry; Photochemistry; Galipinine alkaloid; Biologically active quinoline; Alkaloids; Hydrogenation; Drugs; Metal; Ester||DOI:||10.1002/ejoc.202000957||Language:||en||Status of Item:||Peer reviewed||ISSN:||1434-193X||This item is made available under a Creative Commons License:||https://creativecommons.org/licenses/by-nc-nd/3.0/ie/|
|Appears in Collections:||Chemistry Research Collection|
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