Chemical and Pharmaceutical Bulletin p. 1213 - 1221 (1983)
Update date:2022-09-26
Topics:
Kamijo
Yamamoto
Harada
Iizuka
1-Protected imidazoles, such as 1-acetyl- and 1-benzoylimidazoles, react with various halides, such as benzyl, allyl, α-keto, and alkyl halides, to give 1-protected-3-substituted imidazolium salts in high yields. The resultant imidazolium salts are easily deprotected by treatment with water or alcohols to give the corresponding 1-substituted imidazoles in excellent yields. In this reaction the yields of 1-substituted imidazoles vary with the kinds of halides used and/or with the protecting groups, and the yields increase in the following order: benzyl halides≥allyl halides~α-keto halides>alkyl halides, and acetyl≥benzoyl>ethoxycarbonyl>diethoxymethyl>trimethylsilyl>tosyl.
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Doi:10.1021/ja051790l
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(1945)Doi:10.1021/ja01256a012
(1942)Doi:10.1021/ja01320a058
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(2003)Doi:10.1007/BF00506619
(1982)
