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Chemistry of Natural Compounds

, Volume 6, Issue 6, pp 708–711 | Cite as

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

  • G. A. Frangulyan
  • V. M. Potapov
  • V. L. Sadovskaya
  • L. M. Alekseeva
  • N. N. Suvorov
Article
  • 21 Downloads

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).

     

Keywords

Aniline Aromatic Amine Acetic Anhydride Cotton Effect Amino Derivative 

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • G. A. Frangulyan
  • V. M. Potapov
  • V. L. Sadovskaya
  • L. M. Alekseeva
  • N. N. Suvorov

There are no affiliations available

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