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Synthesis 1987; 1987(3): 290-292
DOI: 10.1055/s-1987-27922
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A Facile Method for the Preparation of 2-Substituted Pyrimidin-4(3H)-ones by a Retro-Diels-Alder Reaction

Géza Stájer* , Angela E. Szabó, Gábor Bernáth, Pál Sohár
  • *Institute of Pharmaceutical Chemistry, University Medical School, H-6720 Szeged, Eötvös u. 6, Hungary
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Publication Date:
12 September 2002 (online)

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diexo-3-Aza-4-oxotricyclo[4.2.1.02,5]non-7-ene (1) reacted with carboximidic esters by ring expansion to yield tricyclic 5,6-dihydropyrimidin-4(3H)-ones 3; when the latter were refluxed in chlorobenzene solution, cyclopentadiene split off to give 2-alkyl, 2-aralkyl-, 2-cycloalkyl and 2-arylpyrimidin-4(3H)-ones 4a-h. This method, which is conveniently carried out in a "one-pot" reaction from 1, provides a good alternative pathway for the preparation of compounds 4.