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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References
M. M. Medvedeva and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 8, 1086 (1982).
V. V. Kuzmenko and A. F. Pozharskii, Adv. Heterocycl. Chem.,53, 85 (1992).
W. Klotzer, H. Baldinger, E. M. Karpitschka, and J. Knoflach, Synthesis, No. 7, 592 (1982).
V. M. Vinogradov, I. L. Dalinger, and S. A. Shevelev, Mendeleev Commun., No. 3, 111 (1993).
V. V. Kuz'menko, A. F. Pozharskii, and V. N. Komissarov, Khim. Geterotsikl. Soedin., No. 1, 93 (1980).
A. Ohsawa H. Arai, H. Ohnishi, T. Itoh, T. Kaihoh, M. Okada, and H. Igeta, J. Org. Chem.,50, 5520 (1985).
A. F. Pozharskii, O. V. Kryshtalyuk, G. G. Aleksandrov, and V. V. Kuz'menko, Khim. Geterotsikl. Soedin., No. 1 (1995) (in press).
Y. Tamura, H. Tsubouchi, E. Doi, and M. Ikeda, Chem. Pharm. Bull.,31, 1378 (1978).
A. F. Pozharskii, V. V. Kuzmenko, M. C. Foces-Foces, A. L. Llamaz-Saiz, R. M. Claramunt, D. Sanz, and J. Elguero, J. Chem. Soc. Perkin II, No. 4, 841 (1994).
A. F. Pozharskii, V. V. Kuz'menko, A. A. Bumber, É. S. Petrov, M. I. Terekhova, N. A. Chikina, and I. M. Nanavyan, Khim. Geterotsikl. Soedin., No. 2, 221 (1989).
H. A. Staab, Angew. Chem.,74, 407 (1962).
A. F. Pozharskii and V. V. Dal'nikovskaya, Usp. Khim.,50, 1559 (1981).
V. A. Anisimova, O. I. Askalepova, K. N. Bagdasarov, and M. S. Chernov'yants, Khim. Geterotsikl. Soedin., No. 3, 345 (1988).
R. M. Claramunt, D. Sanz, J. Catalan, F. Fabero, A. Garcia, C. Foces-Foces, A. L. Llamas-Saiz, and J. Elguero, J. Chem. Soc. Perkin II, 1687 (1993).
Y. Okamoto and T. Ueda, Chem. Pharm. Bull.,25, 3087 (1977).
Additional information
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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DOI: https://doi.org/10.1007/BF01184881