Abstract
Heterocyclic ring cleavage in 20-isoxazolinyl steroids upon treatment with base has been studied. Treatment with sodium dimsyl (dimethylsulfoxide anion) has been found to result in cleavage of the isoxazoline ring and formation of an α,Β-unsaturated ketoxime. The structures of the resulting products are discussed.
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A. A. Akhrem, F. A. Lakhvich, and V. A. Khripach, Khim. Geterotsikl. Soedin., No. 9, 1155 (1981).
A. A. Akhrem, V. A. Khripach, F. A. Lakhvich, M. I. Zavadskaya, O. A. Drachevnova, and I. A. Zorina, Dokl. Akad. Nauk SSSR, 297, 364 (1987).
A. A. Akhrem, V. A. Khripach, R. P. Litvinovskaya, A. V. Baranovskii, and E. V. Borisov, Abstracts of Proceedings, 12th International Conference on Isoprenoids, Beijing (1987), p. 22.
F. A. Lakhvich, T. V. Yankova, E. V. Koroleva, and A. A. Akhrem, Khim. Geterotsikl. Soedin., No. 12, 1698 (1987).
K. Kihira, Y. Morioka, and T. Hoshita, J. Lipid. Res., 22, 1181 (1981).
V. Jager and N. Grand, Angew. Chem., 88, 27 (1976).
G. Timms and E. Wildsmith, Tetrahedron Lett., 195 (1971).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1389–1393, October, 1990.
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Khripach, V.A., Litvinovskaya, R.P., Baranovskii, A.V. et al. Heterocyclic ring cleavage in 20-isoxazolinyl steroids upon treatment with base. Chem Heterocycl Compd 26, 1158–1162 (1990). https://doi.org/10.1007/BF00472191
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DOI: https://doi.org/10.1007/BF00472191