Heterocyclic Compounds
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ChemInform Abstract: Preparation of Uracils via Cycloreversion of Norbornene-Fused Pyrimidinediones.
First published: August 22, 1989
Abstract
The 3-aminonorbornane-2-carboxylic acid (I) reacts with phenyl isocyanate (II) to form the urea (III) which undergoes acid-induced cyclization, yielding the bridged perhydroquinazolinedione (IV).
ChemInform Abstract
The 3-aminonorbornane-2-carboxylic acid (I) reacts with phenyl isocyanate (II) to form the urea (III) which undergoes acid-induced cyclization, yielding the bridged perhydroquinazolinedione (IV). This is also obtained by rearrangement of the β-lactam (VIa). The aminonorbornenecarboxamides (VII) react with 1,1'-carbonyldiimidazole (VIII) to give the unsaturated analogues (IX) of (IV). These perform a thermolytically induced retro-Diels-Alder reaction, producing the uracils (X).
