Synthesis of 1,2,3,4-tetrahydroisoquinolines by microreactor-mediated thermal isomerization of laterally lithiated arylaziridines

Chemistry : a European Journal
Arianna GiovineRenzo Luisi

Abstract

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.

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Citations

Jul 15, 2015·Organic Letters·Nathanael HsuehMichael Shipman
Sep 14, 2016·Organic Letters·Nathanael HsuehMichael Shipman
Jun 2, 2017·Chemical Reviews·Matthew B PlutschackPeter H Seeberger
Apr 19, 2016·Organic & Biomolecular Chemistry·Sonia De AngelisRenzo Luisi
Jul 8, 2016·Chemical Communications : Chem Comm·Leonardo DegennaroRenzo Luisi
Sep 10, 2019·Chemistry : a European Journal·Marco ColellaRenzo Luisi
Apr 14, 2017·Beilstein Journal of Organic Chemistry·Flavio FanelliRenzo Luisi
May 8, 2018·Molecular Diversity·Rabia AkhtarSameera Saleem
May 8, 2021·Chemistry : a European Journal·Kengo InoueKentaro Okano
May 21, 2015·Chemical Reviews·Mohammad HassamWillem A L van Otterlo

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