Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization‐Cyclization Process
Mara Di Filippo, Marcus Baumann
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.
Topics & Concepts
ChemistryIsomerizationTandemQuinolineCascade reactionCombinatorial chemistryPhotoisomerizationCascadeAlkeneFlow chemistryPhotochemistryOrganic chemistryCatalysisChromatographyMaterials scienceComposite materialInnovative Microfluidic and Catalytic Techniques InnovationSynthesis and Catalytic ReactionsChemical Synthesis and Analysis