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Synthesis 1989; 1989(12): 908-911
DOI: 10.1055/s-1989-27428
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Nucleophile Substitution an 6H-1,2-Oxazinen über Azapyrylium-lonen

Reinhold Zimmer* , Hans-Ulrich Reißig
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Federal Republic of Germany
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Publication Date:
02 May 2002 (online)

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Nucleophilic Substitution of 6H-1,2-Oxazines via Azapyrylium Ions In the presence of Lewis-acids, the 6-methoxy group of 6-methoxy-6H-1,2-oxazines is smoothly substituted by nucleophiles to give a variety of new 6-substituted 6H-1,2-oxazines. Azapyrylium ions (1,2-oxazin-1-ium ions) are suggested to be the intermediates involved in this regioselective reaction which proceeds most satisfactoryly with silylated compounds or electron-rich arenes as nucleophilic components.

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