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Report | Regular issue | Vol 23, No. 7, 1985, pp.1759-1764
Published online, 1st January, 1970
DOI: 10.3987/R-1985-07-1759
Synthesis of 2-Acyl-1-methyl-1H-imidazoles and Reactivity of the Acyl Group

Shunsaku Ohta, Satoshi Hayakawa, Hiroki Moriwaki, Shin-ichi Tsuboi, and Masao Okamoto*

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan

Abstract

2-Alkanoyl- and 2-aroyl-1-methyl-1H-imidazoles (3) were prepared in good yields by treating 1-acylpyrrolidine (1) with 2-lithio-1-methyl-1H-imidazole (2) at -78°C. Although 2-benzoyl-1-methyl-1H-imidazole (3a) was stable under n-Pr-NH2/80°C/10h; 2% K2CO3/aq. CH3OH/80°C /10h; 20% H2SO4/80°C/10h; CF3COOH/r.t./17h, it was hydrolysed into benzoic acid and 1-methyl-1H-imidazole by heating in 1.3N-NaOH - aq. ethanol at 80°C for 30h. The acyl group of 3 was activated by conversion to the corresponding imidazolium salt (4), which could react with various nucleophiles.