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Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization‐Cyclization Process
Author(s) -
Di Filippo Mara,
Baumann Marcus
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000957
Subject(s) - chemistry , isomerization , tandem , quinoline , cascade reaction , combinatorial chemistry , photoisomerization , cascade , alkene , flow chemistry , photochemistry , organic chemistry , catalysis , materials science , chromatography , composite material
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.