Abstract
Abstract The reactions of 3-acyl-2-azabicyclo[2.2.1]hept-5-enes with phenyl isocyanate, phenyl isothiocyanate, and ethoxycarbonyl isothiocyanate followed by cyclization reactions under basic conditions respectively provided a hydantoin, a thiohydantoin, and a 1,3-dihydro-2H-imidazole-2-thione incorporated with the azabicyclic skeleton. Treatment of the imidazolethione with Raney nickel gave a phenyl-substituted imidazole fused with 2-azabicyclo[2.2.1]hept-2-ene. The effect of annulation on the 13C NMR of the imidazole ring is discussed.
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