Regioselective Nitro Group Substitution. Synthesis of Isomeric 4-Amino-5-nitro-and 5-Amino-4-nitroimidazoles

L Zaprutko, J Zwawiak, D Olender, A Gzella

Index: Zaprutko, Lucjusz; Zwawiak, Justyna; Olender, Dorota; Gzella, Andrzej Heterocycles, 2012 , vol. 85, # 9 p. 2197 - 2211

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Abstract

Abstract-On the basis of the reactions between 4, 5-dinitroimidazole derivatives (1-methyl-4, 5-dinitroimidazole, l, 2-dimethyl-4, 5-dinitroimidazole and ethyl 2-(4, 5-dinitroimidazol—l-yl) acetate) and cyclic amines (morpholine, piperidine or pyrrolidine) in mild conditions (THF or ethanolic solution), the order of nitro group substitution has been discovered for the first time. The influence of the solvent, steric effects and possibility of hydrogen bonds formation on ...