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Synthesis 1994; 1994(4): 405-410
DOI: 10.1055/s-1994-25487
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Dihalogentriphenylphosphorane in der Heterocyclensynthese, 29.1 Eine einfache Synthese von Pteridin-4-onen aus 3-Amino-2-pyrazincarbonsäuremethylester und Pyrazino[3,1]oxazin-4-onen

Heinrich Wamhoff* , Elmar Kroth
  • *lnstitut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany
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Publication Date:
17 September 2002 (online)

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Dihalogentriphenylphosphoranes in the Synthesis of Heterocycles, 29.1 A Simple Synthesis of Pteridin-4-ones, from Methyl 3-Amino-2-pyrazinecarboxylate and Pyrazino[3,1]oxazin-4-ones Methyl 3-amino-2-pyrazinecarboxylate(3) affords the synthetically useful 3-aroylaminopyrazin-2-carboxylates 5a-f with aroyl chlorides, which are converted with dibromotriphenylphosphorane into 2-arylpyrazino[2,3-d][3,1]oxazin-4-ones 6a-f. Nucleophilic attack at the carbonyl function of these oxazinones results in ring cleaved amides which can be recyclized with dibromotriphenylphosphorane to afford 2-arylpteridin-4-ones 7a-f.