Abstract
A number of 5-nitro-N,N-diphenylhydrazinopyrimidines were synthesized. Free radicals were obtained by oxidation of these compounds with PbO2. The stabilities of 5-nitro-4-pyrimidinylhydrazyl radicals are close to the stability of the α,α-diphenyl-β-2,4-dinitrophenylhydrazyl radical. The structures of the compounds obtained were confirmed by the UV, IR, PMR, and EPR spectra.
Similar content being viewed by others
Literature cited
É. G. Rozantsev and V. D. Sholle, The Organic Chemistry of Free Radicals [in Russian], Khimiya, Moscow (1979).
V. M. Cherkasov, G. S. Tret'yakova, and N. N. Aleksandrova, Ukr. Khim. Zh., 36, 694 (1970).
H. C. van der Plas, H. Jongejan, and A. Koudijs, J. Heterocycl. Chem., 15, 485 (1978).
T. A. Turney, Mechanisms of Redox Reactions [Russian translation], Mir, Moscow (1968), p. 66.
R. W. Baldock, P. Hudson, A. R. Katritzky, and F. Soti, J. Chem. Soc., Perkin I, 1422 (1974).
A. T. Balaban, P. T. Frangopol, M. Marculescu, and J. Bally, Tetrahedron, 13, 258 (1961).
E. C. Taylor, J. W. Barton, and W. W. Paudler, J. Org. Chem., 26, 4961 (1961).
N. Whittaker, J. Chem. Soc., 1565 (1951).
R. O. Robbin, P. S. Winnek, and J. P. English, J. Am. Chem. Soc., 64, 567 (1942).
W. R. Boon, W. G. M. Jones, and G. R. Ramage, J. Chem. Soc., 96 (1951).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1545–1549, November, 1980.
Rights and permissions
About this article
Cite this article
Boldyrev, I.V., Polumbrik, O.M., Markovskii, L.N. et al. Synthesis of 5-nitro-N,N-diphenylhydrazinopyrimidines and investigation of their free radicals. Chem Heterocycl Compd 16, 1179–1183 (1980). https://doi.org/10.1007/BF00504119
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00504119