SYNTHESIS OF 2,5-DILITHIO-1-METHYLIMIDAZOLE

Authors
SHAPIRO G MARZI M
Citation
G. Shapiro et M. Marzi, SYNTHESIS OF 2,5-DILITHIO-1-METHYLIMIDAZOLE, Tetrahedron letters, 34(21), 1993, pp. 3401-3404
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
21
Year of publication
1993
Pages
3401 - 3404
Database
ISI
SICI code
0040-4039(1993)34:21<3401:SO2>2.0.ZU;2-6
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-mediyl-imidazole (4). Reaction of 4 with one equivalent of DMF occurs selectively at the C5 position to give 1-methyl ole-5-carboxaldehyde (1).