Tetrahedron letters

Synthesis of 2, 5-Dilithio-1-methylimidazole

G Shapiro, M Marzi

Index: Shapiro, Gideon; Marzi, Martin Tetrahedron Letters, 1993 , vol. 34, # 21 p. 3401 - 3404

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Citation Number: 25

Abstract

Abstract 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 ...

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