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

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Title: Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process
Authors: Di Filippo, MaraBaumann, Marcus
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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: QuinolineTetrahydroquinolineFlow chemistryPhotochemistryGalipinine alkaloidBiologically active quinolineAlkaloidsHydrogenationDrugsMetalEster
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:
Appears in Collections:Chemistry Research Collection

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