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

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-aminoimidazole 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.

How to Cite
Vinogradova, O. V.; Kryshtalyuk, O. V.; Rudnev, M. I.; Pozharskii, A. F.; Kuz'menko, V. V. Chem. Heterocycl. Compd. 1994, 30, 1182. [Khim. Geterotsikl. Soedin. 1994, 1364.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01184881