IMIDAZOLE DERIVATIVES CONTAINING POTENTIALLY LABILE GROUPS ON THE N(1) ATOM 8. SYNTHESIS OF N-AMINOIMIDAZOLES VIA 1-AMINO-3-METHOXYMETHYLIMIDAZOLIUM AND 1-AMINO-3-ACETYLIMIDAZOLIUM SALTS

Article abstract of DOI:10.1007/BF01184881

When O-picrylhydroxylamine is reacted with 1-methoxymethyl and 1-acetyl derivatives of imidazole, benzimidazole, 2-cyanomethylbenzimidazole, and perimidine, 1-amino-3-R-imidazolium-, -benzimidazolium, and -perimidinium picrates are formed (R = CH3OCH2, CH3CO).Their subsequent hydrolysis (spontaneous in the case of the N-acetyl derivatives) results in the elimination of the labile R substituent and the formation of the corresponding N-amino-imidazole or -perimidine.In a number of cases this is a more convenient method for their synthesis than the direct amination of NH-heterocycles in alkaline medium.