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DOI: 10.1055/s-2003-38067
A Convenient Synthesis of 4(5)-Alkylacyl-1H-imidazoles from 4(5)-Imidazolecarboxaldehyde
Publication History
Publication Date:
21 March 2003 (online)
Abstract
A convenient synthesis of 4(5)-acyl-1H-imidazoles from 4(5)-imidazolecarboxaldehyde without N-protecting group is described. 4(5)-Cyanoimidazole could be synthesized from commercially available 4(5)-imidazolecarboxaldehyde in one-pot. Treatment of 4(5)-cyanoimidazole with various alkylmagnesium bromides followed by addition of aqueous sulfuric acid afforded 4(5)-acyl-1H-imidazoles in good yield.
Key words
Grignard reaction - ketones - nitriles - alkylations
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References
During the dropwise addition of isopropylmagnesium bromide in THF to a solution of 4(5)-cyanoimdazole(2) in THF, the reaction mixture solidified to a cake and could not be stirred. This procedure is unsuitable for large-scale synthesis.