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The first application of an imidazole o-quinodimethane in Diels-Alder reactions leading to the synthesis of benzimidazoles
Authors:Constantinos Neochoritis
Affiliation:Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Macedonia, Greece
Abstract:An efficient procedure for the generation of the imidazole-4,5-quinodimethane intermediate 4 from 2-bromo-4,5-bis(bromomethyl)imidazole derivative 3 in boiling toluene in the presence of 18-crown-6 is described. o-Quinodimethane 4 was captured for the first time by several symmetrically and unsymmetrically substituted dienophiles to afford the corresponding Diels-Alder benzimidazole adducts.
Keywords:Imidazole o-quinodimethanes   Benzimidazoles   Diels-Alder reactions
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