6533b82afe1ef96bd128cafe

RESEARCH PRODUCT

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

Antal CsámpaiGéza StájerAngela E. SzabóPál SohárReijo Sillanpää

subject

Inorganic Chemistrychemistry.chemical_compoundchemistryFuranOrganic ChemistryThermal decompositionDiels alderDiastereomerOrganic chemistryNuclear magnetic resonance spectroscopyRetro-Diels–Alder reactionSpectroscopyAnalytical Chemistry

description

Abstract 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.

yearjournalcountryeditionlanguage
2006-02-01Journal of Molecular Structure
https://doi.org/10.1016/j.molstruc.2005.09.011