Abstract
The reaction of 4-oxo-1,3-benz- and -naphthoxazinium perchlorates with hydroxylamine leads to 5-(o-hydroxyaryl)-1,2,4-oxadiazoles rather than to 3-(o-hydroxyaryl)-1,2,4-oxadiazoles, as was previously assumed. The structure of the compounds obtained was proved by alternative synthesis, as well as by mass spectrometry and comparison of the experimentally found and calculated dipole moments and Kerr constants of the possible structures of the o-hydroxyaryl-1,2,4-oxadiazoles.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
Yu. I. Ryabukhin, Summaries of Papers Presented at the 2nd All-Union Conference on the Chemistry of Azines [in Russian], Sverdlovsk (1985), p. 31.
Yu. I. Ryabukhin, G. N. Dorofeenko, and V. V. Mezheritskii,Khim. Geterotsikl. Soedin., No. 2, 280 (1975).
O. Yu. Ryabukhina, Yu. I. Ryabukhin, B. S. Luk'yanov, and G. N. Dorofeenko,Khim. Geterotsikl. Soedin., No. 12, 1611 (1979).
A. V. Iogansen,Hydrogen Bonding [in Russian], Nauka, Moscow (1981), p. 112.
G. Emsley, J. Finney, and L. Sutcliff,High-Resolution NMR Spectroscopy [Russian translation], Vol. 1, Mir, Moscow (1986), p. 514.
Yu. I. Ryabukhin, L. N. Faleeva, M. O. Gorbunova, T. V. Kovaleva, I. E. Uflyand, and V. N. Sheinker,Zh. Org. Khim.,24, No. 9, 1990 (1988).
S. B. Bulgarevich, T. A. Yusman, O. Yu. Ryabukhina, N. I. Dorokhova, Yu. I. Ryabukhin, G. N. Dorofeenko, and O. A. Osipov,Zh. Obshch. Khim.,51, No. 6, 1418 (1981).
G. N. Dorofeenko, Yu. I. Ryabukhin, S. B. Bulgarevich, V. V. Mezheritskii, and O. Yu. Ryabukhina,Zh. Org. Khim.,13, No. 11, 2459 (1977).
A. Spilker,Ber.,22, 2767 (1889).
M. J. Dimisdale,J. Heterocycl. Chem.,18, No. 1, 37 (1981).
K. Clark,J. Chem. Soc., 4251 (1954).
H. Zimmer,Ber.,22, 3140 (1889).
R. Elderfield (ed.),Heterocyclic Compounds [Russian translation], Vol. 7, Moscow (1965), p. 391.
D. Barton and U. D. Ollis (eds.),General Organic Chemistry [Russian translation], Vol. 9, Khimiya, Moscow (1985), p. 519.
S. B. Bulgarevich, O. A. Osipov, V. S. Bolotnikov, T. V. Lifintseva, V. N. Sheinker, and A. D. Garnovskii,Dokl. Akad. Nauk SSSR,224, No. 4, 847 (1975).
S. B. Bulgarevich, V. S. Bolotnikov, V. N. Sheinker, O. A. Osipov, and A. D. Garnovskii,Zh. Obshch. Khim.,45, No. 8, 1821 (1975).
W. C. Macrodt, A. Waldley, P. A. Curnuck, N. L. Owen, and J. Sheridan,Chem. Commun., No. 19, 692 (1966).
M. H. Palmer, R. H. Findlay, and A. J. Gaskell,J. Chem. Soc., Perkin Trans. 2, No. 4, 420 (1974).
V. I. Ivanskii,The Chemistry of Heterocyclic Compounds [in Russian], Vyssh. Shkola, Moscow (1978), p. 186.
V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov,Dipole Moments in Organic Chemistry [in Russian], Khimiya, Leningrad (1968).
S. B. Bulgarevich, S. I. Adamova, D. Ya. Movshovich, A. A. Polunin, V. A. Kogan, and O. A. Osipov,Zh. Obshch. Khim.,49, No. 1, 199 (1979).
A. Mustafa and A. E. A. Hassan,J. Am. Chem. Soc.,79, 3846 (1957).
I. E. Uflyand, Yu. I. Ryabukhin, M. O. Gorbunova, and V. N. Sheinker,Izv. SKNTs VSh. Estestvennye Nauki, No. 1, 78 (1990).
K. V. Vatsuro and G. L. Mishchenko,Name Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 10.
I. E. Uflyand, Yu. I. Ryabukhin, B. D. Vysotskii, V. N. Askalepov, and V. P. Kurbatov,Koordinats. Khim.,8, No. 7, 922 (1982).
S. B. Bulgarevich, V. N. Sheinker, O. A. Osipov, A. D. Garnovskii, and A. S. Kuzharov,Zh. Obshch. Khim.,44, 1994 (1974).
T. Fujita,J. Am. Chem. Soc.,79, No. 10, 2471 (1957).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 540–549, April, 1992.
Rights and permissions
About this article
Cite this article
Ryabukhin, Y.I., Eliseeva, A.Y., Suzdalev, K.F. et al. Synthesis and study of the structure of o-hydroxyaryl-1,2,4-oxadiazoles. Chem Heterocycl Compd 28, 454–463 (1992). https://doi.org/10.1007/BF00767011
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00767011