A Convenient Synthesis of 4(5)-Alkylacyl-1H-imidazoles from 4(5)-Imidazolecarboxaldehyde

Jun-ichi Kawakami; Kazuhiro Kimura; Masayoshi Yamaoka

doi:10.1055/s-2003-38067

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A Convenient Synthesis of 4(5)-Alkylacyl-1H-imidazoles from 4(5)-Imidazolecarboxaldehyde

Jun-ichi Kawakami*, Kazuhiro Kimura, Masayoshi Yamaoka
Chemical Development Laboratories, Takeda Chemical Industries, Ltd., 2-17-85 Jusohonmachi, Yodogawa-ku, Osaka 532-8686, Japan
e-Mail: Kawakami_Junichi@takeda.co.jp;

Abstract

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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

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