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Synthesis 1991; 1991(9): 765-768
DOI: 10.1055/s-1991-26570
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Diels-Alder Reactions of 6-Alkyl-3,5-dichloro-2H-1,4-oxazin-2-ones with Alkynes: Synthesis of 3,5-Disubstituted 2,6-Dichloropyridines

Lieven Meerpoel* , Geert Deroover, Koen Van Aken, Gerrit Lux, Georges Hoornaert
  • *Laboratorium voor Organische Synthese, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium
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Publication Date:
29 April 2002 (online)

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The Diels-Alder reaction of 6-alkyl-3,5-dichloro-2H-1,4-oxazin-2-ones 1 with different types of acetylenic compounds 2 is shown to be a versatile method for the generation of variously substituted 2,6-dichloropyridines. In most cases a high degree of regioselectivity and a high yield of 3,5-disubstituted 2,6-dichloropyridines 3 is obtained.