Synthesis of 1,2,3,4-Tetrahydroisoquinolines by Microreactor-Mediated Thermal Isomerization of Laterally Lithiated Arylaziridines

Authors

  • Dr. Arianna Giovine,

    1. Department of Pharmacy, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari (Italy), Fax: (+39) 080-5442539
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  • Dr. Biagia Musio,

    1. Department of Pharmacy, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari (Italy), Fax: (+39) 080-5442539
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  • Dr. Leonardo Degennaro,

    1. Department of Pharmacy, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari (Italy), Fax: (+39) 080-5442539
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  • Dr. Aurelia Falcicchio,

    1. Istituto di Cristallografia (IC-CNR), Via Amendola 122/o, 70125 Bari (Italy)
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  • Dr. Aiichiro Nagaki,

    1. Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, University of Kyoto, Nishikyo-ku, Kyoto, 615-8510 (Japan)
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  • Prof. Jun-ichi Yoshida,

    Corresponding author
    1. Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, University of Kyoto, Nishikyo-ku, Kyoto, 615-8510 (Japan)
    • Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, University of Kyoto, Nishikyo-ku, Kyoto, 615-8510 (Japan)
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  • Prof. Renzo Luisi

    Corresponding author
    1. Department of Pharmacy, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari (Italy), Fax: (+39) 080-5442539
    • Department of Pharmacy, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari (Italy), Fax: (+39) 080-5442539
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Abstract

original image

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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