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Synthesis 1990; 1990(10): 905-908
DOI: 10.1055/s-1990-27049
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A General Synthesis of 3,5-Dihalo-2H-1,4-oxazin-2-ones from Cyanohydrins

Lieven Meerpoel* , Georges Hoornaert
  • *Laboratorium voor Organische Synthese, K. U. Leuven, Celestijnenlaan 200F, B-3030 Leuven, Belgium
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Publication Date:
17 September 2002 (online)

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In a novel approach starting from O-trimethylsilyl protected or unprotected cyanohydrins and oxalyl chloride or bromide, a series of unknown 6-substituted 3,5-dihalo-2H-1,4-oxazin-2-ones were prepared. The method was shown to be efficient for various types of cyanohydrins; however cyclization was not obtained with cyanohydrins containing bulky substituents, electron-rich aryl or heteroaryl groups. A mechanism is proposed.