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).
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.
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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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
- Aromatic Amine
- Acetic Anhydride
- Cotton Effect
- Amino Derivative