New synthesis of 2??nitroimidazoles

DP Davis, KL Kirk, LA Cohen

Index: Davis, Dwight P.; Kirk, Kenneth L.; Cohen, Louis A. Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 253 - 256

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Citation Number: 29

Abstract

Abstract 1-Triphenylmethylimidazoles are treated with n-butyllithium in tetrahydrofuran at 0 to form the 2-lithio derivatives. The latter species react with n-propyl nitrate to give l-trityl-2- nitroimidazoles which, after acid hydrolysis, provide the corresponding 2-nitroimidazoles. 2- Nitroimidazole was obtained from imidazole in overall yields of 27–35% 4-methyl-2- nitroimidazole was obtained in 40% overall yield from 4-methyl-imidazole. Imidazole-4, 5- ...