Derivatives of the androstane series
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1. The synthesis of 17β-hydroxyandrostano[3,2-c]pyrazole and of cholestano[3,2-c]pyrazole has been effected by the reaction of the corresponding 2-hydroxymethylene-3-oxosteroids with hydrazine hydrate.
2. The mechanism of the formation of these pyrazoles has been studied. It has been shown that the reaction takes place in two stages, regardless of the substituent at C17 of the steroid molecule, with the formation of the 2-hydroxymethylene-3-hydrazone and its dehydration to form the pyrazole derivative.
KeywordsPyrazole Hydrazones Primary Amine Hydrazine Hydrate Anabolic Steroid
- 2.I. I. Kuz'menko, L. N. Volovel'skii, and N. V. Novikova, ZhOKh, 39, 447, 1969.Google Scholar
- 3.L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], Moscow, 356, 1963.Google Scholar
- 4.R. O. Clinton, R. L. Clarke, F. W. Stonner, A. J. Manson, K. F. Jennings, and D. K. Phillips, J. Org. Chem., 27, 2805, 1962.Google Scholar
- 5.A. P. Ambler, in: Physical Methods in Heterocyclic Chemistry, ed. A. R. Katritzky [Russian translation], Khimiya, Moscow-Leningrad, 533, 536, 1966.Google Scholar
- 6.L. N. Volovel'skii and G. V. Knorozova, ZhPKh, 35, 2580, 1962.Google Scholar
- 7.L. N. Volovel'skii and A. B. Simkina, ZhOKh, 37, 1571, 1967.Google Scholar