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A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines

Authors

  • Bernhard Gutmann,

    1. Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Dr. Jean-Paul Roduit,

    1. Microreactor Technology, Lonza AG, CH-3930 Visp (Switzerland)
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  • Dr. Dominique Roberge,

    Corresponding author
    1. Microreactor Technology, Lonza AG, CH-3930 Visp (Switzerland)
    • Microreactor Technology, Lonza AG, CH-3930 Visp (Switzerland)
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  • Prof. Dr.  C. Oliver Kappe

    Corresponding author
    1. Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz (Austria), Fax: (+43) 316-380-9840
    • Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz (Austria), Fax: (+43) 316-380-9840
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Abstract

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Harnessing hydrazoic acid in flow! 2-Oxazolines can be ring-opened in a very efficient manner by treatment with in situ generated hydrazoic acid. Despite the toxic and explosive nature of hydrazoic acid, this process can be conducted safely in a continuous-flow format with residence times as short as 5 min at 130 °C (see scheme).

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