Abstract
An efficient procedure for the trapping of an imidazole-4,5-quinodimethane intermediate 3 with quinones in boiling toluene and in the presence of 18-crown-6 is described. In all cases the fully aromatized imidazole-naphthoquinone derivatives were isolated as the main reaction products in satisfactory yields. However, in the case of benzo- and naphthoquinone, aromatized products were also isolated, in which the bromine in the 2-imidazole position was -replaced by hydrogen, whereas in the case of the asymmetrical 2-phenylbenzoquinone and 5,8-quinoline dione inseparable regioisomeric mixtures were formed.
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