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Flow chemistry: A flow-microreactor-mediated synthesis of 1,2,3,4-tetrahydroisoquinolines (THIQs) is reported (see scheme). Starting from a laterally lithiated aziridine, a tetrahydroisoquinoline lithiated at C4 was generated by thermally induced isomerization. Because the reaction temperature is a crucial parameter, the exquisite thermal control possible in a flow-microreactor system allowed for fast, efficient, and highly reproducible synthesis of functionalized aziridines or THIQs. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Arianna Giovine, Biagia Musio, Leonardo Degennaro, Aurelia Falcicchio, Aiichiro Nagaki, Jun-ichi Yoshida, Renzo Luisi. Synthesis of 1,2,3,4-tetrahydroisoquinolines by microreactor-mediated thermal isomerization of laterally lithiated arylaziridines. Chemistry (Weinheim an der Bergstrasse, Germany). 2013 Feb 4;19(6):1872-6

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PMID: 23322634

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