The regioselective synthesis of 1-benzyl-and 1-methyl-4vinylimidazole from 4,5-diiodoimidazole is described.Their Diels-Alder reactions with N-phenylmaleimide provide a variety of adducts, including the anticipated enamine and the corresponding aromatized isomer.However, additional products including ene adducts, a bis Diels-Alder adduct and oxidation products were isolated.
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Lovely et al. (2003) studied this question.
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