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Paper | Regular issue | Vol 68, No. 7, 2006, pp.1359-1370
Published online, 30th May, 2006
DOI: 10.3987/COM-06-10726
An Efficient and Convenient Method for Synthesis of 1-Substituted Imidazoles

Chun Min Lin, Fung Fuh Wong,* Jiann-Jyh Huang, and Mou-Yung Yeh

*Sustainable Environment Research Center, National Cheng Kung University, No. 500, Sec. 3, An-ming Rod., Tainan City, 709, Taiwan, R.O.C.

Abstract

A convenient method for the synthesis 1-substituted imidazoles was developed by the reaction of α-bromoketone with lithium imidazolide. The reaction gave the desired products in improved yields without the formation of 1,3-disubstituted imidazolium salts. Treatment of bromoacetaldehyde ethylene acetal, 2-(bromomethyl)tetrahydro-2H-pyran, and N-(bromomethyl)phthalimide with lithium imidazolide also gave the corresponding 1-substituted imidazole in good to excellent yields. Direct reaction of α-bromoketone with imidazole as control experiment afforded undesired 1,3-disubstituted imidazolium salts with the desired mono-substituted products.