Abstract
Novel imidazole-oxadiazole ring interconversions (transformations) accompanying nucleophilic amination of 4-nitroimidazoles by hydroxylamine or 4-amino-1, 2, 4-triazole are described with suggestions concerning mechanisms of the reactions.
Similar content being viewed by others
References
A. R. Katritzky, M. Karelson, and N. Malhotra, Heterocycles,32, 127 (1991).
M. R. Gimmett, in: Comprehensive Heterocyclic Chemistry: Imidazoles and Their Benzo Derivatives: Reactivity, A. R. Katritzky and C. W. Rees (eds.), Pergamon Press Oxford-New York-Toronto-Sydney-Paris-Frankfurt (1985), Vol. 5, p. 406.
B. Cavalleri, P. Bellani, and G. Lancini, J. Heterocycl. Chem.,10, 357 (1973).
J. Suwinski and E. Salwinska, Tetrahedron,50, 5741 (1994).
J. Suwinski and W. Szczepankiewicz, Arch. Pharm. (Weinheim),325, 317 (1992).
J. Suwinski, K. Swierczek, and T. Glowiak, Tetrahedron,49, 5339 (1993).
J. Suwinski, W. Pawlus, E. Salwinska, and K. Sierczek, Heterocycles,37, 1511 (1994).
M. W. Miller, H. L. Rowers Jr., R. V. Kasubick, and A. R. English, J. Med. Chem.,13, 849 (1970).
G. E. Adams, E. D. Clarke, I. R. Flockhart, R. S. Jacobs, D. S. Sehmi, I. J. Stratford, P. Wardman, M. E. Watts, J. Patrick, R. G. Wallace, and C. E. Smithen, Int. J. Radiat. Biol.,35, 133 (1978).
V. Surcjic, T. Fajdiga, M. Japelj, and P. Rems, J. Heterocycl. Chem.,6, 53 (1969).
A. R. Katritzky and K. S. Laurenzo, J. Org. Chem.,53, 3978 (1988).
J. Suwinski and P. Wagner, Tetrahedron, in press.
K. Tiemann and P. Kruger, Ber.,17, 1685 (1884).
Additional information
Institute of Organic Chemistry and Technology Silesian Technical University, Krzywoustego 4, 44-100 Gliwice, Poland.Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1214–1221, September, 1996. Original article submitted May 20, 1996.
Rights and permissions
About this article
Cite this article
Suwinski, J., Swierczek, K. Transformations of the imidazole ring in 1-alkyl and 1-aryl-4-nitroimidazoles following the attack of hydroxylamine or 4-amino-1,2,4-triazole. Chem Heterocycl Compd 32, 1040–1046 (1996). https://doi.org/10.1007/BF01164709
Issue Date:
DOI: https://doi.org/10.1007/BF01164709