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Steroids XLII. The reaction of 16α, 17α-epoxypregnenolone with aromatic amines

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Summary

  1. 1.

    The reaction of 16α, 17α-expoxypregnenolone with primary aromatic a amines (aniline, p-toluidine, and p-anisidine) has been studied. The reaction products are amino derivatives of D-homosteroids: 16β-anilino-(IIa), 16β-p-toluidino- (IIb), and 16β-p-anisidino-3β, 17aα-dihydroxy-17aβ-methyl-D-homoandrost-5-en-17-one (IIc).

  2. 2.

    The structure and configuration of the compounds (IIa, b, and c) obtained have been shown by a series of chemical reactions and by physicochemical methods.

  3. 3.

    The acetylation of IIa with acetic anhydride in pyridine leads to the formation of 16β-anilino-3β, 17aα-diacetoxy-17aβ-methyl-D-homoandrost-5-en-17-one (III).

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Literature cited

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Additional information

Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry. Lomonosov Moscow State University. Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 698–702, November–December, 1970.

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Frangulyan, G.A., Potapov, V.M., Sadovskaya, V.L. et al. Steroids XLII. The reaction of 16α, 17α-epoxypregnenolone with aromatic amines. Chem Nat Compd 6, 708–711 (1970). https://doi.org/10.1007/BF00565338

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Keywords

  • Aniline
  • Aromatic Amine
  • Acetic Anhydride
  • Cotton Effect
  • Amino Derivative