Journal of Organic Chemistry p. 5685 - 5689 (1988)
Update date:2022-08-05
Topics:
Katritzky, Alan R.
Rewcastle, Gordon W.
Fan, Wei-Qiang
The lithiation of N-(dialkylamino)methyl (aminal) derivatives of imidazole, benzimidazole, and pyrazole (themselves readily available from parent heterocycles, formaldehyde, and a secondary amine) occurs smoothly at 2-, 2-, and 5-positions, respectively, upon treatment with n-butyllithium in ether or tetrahydrofuran.Reaction with electrophiles, and subsequent facile acid-catalyzed hydrolysis of the protecting group, provides 2-substituted imidazoles, 2-substituted benzimidazoles, and 3(5)-substituted pyrazoles in good overall yields.
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