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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

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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-heterocyles in alkaline medium.

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Rostov State University, Rostov-on-Don, 344006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1364–1368, October 1994. Original article submitted October 21, 1994.

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Vinogradova, O.V., Kryshtalyuk, O.V., Rudnev, M.I. et al. 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. Chem Heterocycl Compd 30, 1182–1186 (1994). https://doi.org/10.1007/BF01184881

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