Preparation of noncondensed 2-substituted 1-methylimidazoles via ipso substitution reaction on 2-sulfinyl or 2-sulfonyl derivatives of 4,5-disubstituted 1-methylimidazoles

We now report the first examples of the utility of 2-(methylsulfinyl)- and 2-(methylsulfonyl) imidazoles as substrates for ipso substitution reactions using anionic nucleophiles (alkoxide, azide, thiolate) to provide the corresponding 2-substituted imidazole in moderate to high yields. Particularly important to this paper are the state of activation of the heterocyclic substrate and the effect of the leaving group on reactivity