Facile conversion of 4 (5)-nitro-5 (4)-methylimidazoles into 4 (5)-nitro-5 (4)-cyanoimidazoles

RS Hosmane, A Bhan, ME Rauser

Index: Hosmane, Ramachandra S.; Bhan, Anila; Rauser, Michael E. Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5892 - 5895

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Citation Number: 21

Abstract

alkylation3 of heterocycles by DMF acetals4 is well estab-lished. The absence of any acid catalyst, coupled with the observed nonregiospecific alkylation of the imidazole ring, suggests the intermediacy of the imidate cation 9 and the resonance-delocalized imidazole anion 10 in this reaction. All the starting materials employed in this investigation were prepared from the commercially available5 4 (5)-methylimidazole. Nitration6 of the latter ( ...