A retro Diels-Alder method for the preparation of pyrrolo[1,2-a] pyrimidinediones from diexo-aminooxanorbornenecarboxamide

Géza Stájer, Angela E. Szabó, Pál Sohár, Antal Csámpai, Reijo Sillanpää

Research output: Contribution to journalArticle

20 Citations (Scopus)


Through the reactions of diexo-3-amino-7-oxanorbornene-2-carboxamide 1 with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2-4 in a retro Diels-Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds, the 1-aroylhexahydroisoindol-3-ones (5-8) were formed; the phenyl-substituted derivatives gave diastereomeric mixtures. The structures of the new compounds were established by NMR spectroscopy and, for 3 and 6, also by single-crystal X-ray structure determination.

Original languageEnglish
Pages (from-to)239-243
Number of pages5
JournalJournal of Molecular Structure
Issue number1-3
Publication statusPublished - Feb 20 2006



  • Aminooxanorbornenecarboxamide
  • Isoindolone
  • NMR
  • Pyrrolopyrimidinediones
  • Retro Diels-Alder reaction
  • X-ray

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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