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

File(s)
FileDescriptionSizeFormat
Download Quinoline EurJOC post print.pdf1.04 MB
Author(s)
Di Filippo, Mara 
Baumann, Marcus 
Uri
http://hdl.handle.net/10197/12603
Date Issued
22 October 2020
Date Available
09T16:03:37Z November 2021
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.
Sponsorship
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 q...

  • Alkaloids

  • Hydrogenation

  • Drugs

  • Metal

  • Ester

DOI
10.1002/ejoc.202000957
Language
English
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/
Owning collection
Chemistry Research Collection
Scopus© citations
18
Acquisition Date
Jan 29, 2023
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Views
365
Acquisition Date
Jan 29, 2023
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Downloads
88
Last Week
5
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5
Acquisition Date
Jan 29, 2023
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