Abstract
Reaction of 2-unsubstituted 1H-imidazole 3-oxides with isocyanates, isothiocyanates, and dimethyl acetylenedicarboxylate led to the formation of 2-functionalized imidazole derivatives. Stepwise reaction mechanisms via zwitterionic intermediates are proposed. The intermediate [3+2] cycloadducts stabilize via extrusion of COX or ring opening.
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