Tetrahedron Letters p. 3401 - 3404 (1993)
Update date:2022-08-04
Topics:
Shapiro, Gideon
Marzi, Martin
C5 to C2 position migrations of 2-trialkylsilyl and thiophenyl groups have been observed upon lithiation at the C5-position of corresponding C2-substituted 1-methylimidazoles.Double bromine-lithium exchange of 1-methyl-2,5-dibromoimidazole (5) affords a facile, quantitative and unequivocal synthesis of 2,5-dilithio-1-methyl-imidazole (4).Reaction of 4 with one equivalent of DMF occurs selectively at the C5 position to give 1-methylimidazole-5-carboxaldehyde.
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