Synthesis of 5-Halo-4H-1,3-oxazine-6-amines by a Copper-Mediated Domino Reaction

Authors

  • Prof. Dr. A. Stephen K. Hashmi,

    Corresponding author
    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
    • Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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  • Dipl.-Chem. Andreas M. Schuster,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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  • Marc Zimmer,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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  • Dr. Frank Rominger

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
    2. Crystallographic investigation.
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Abstract

original image

Three become one! In one copper-mediated step, three simple components, including a propargylcarboxamide, a protected amine, and a source of chloride, assemble to give highly functionalized oxazines, which are interesting building blocks for the synthesis of other aminooxazine derivatives (see scheme; R1=range of aryl or alkyl groups, R2=alkyl, EWG=electron-withdrawing group).

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