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Synthesis and properties of dithioacetals of conformationally constrainedα-acyl-β-aminovinyl ketones of the 8-azasteroid

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have the reaction of α-acyl-β-aminovinyl of the 8-azasteroid series with ethanedithiol. The occurrence and orientation of the reaction are determined by structural and steric factors. As applied to derivatives of 8-azasteroids of the D-homo series, the reaction is irreversible and consequently the dithioacetal derivatives of this series are easily hydrolysed under acid and base conditions. Desulfurization over Raney nickel of the 17-dithioacetal derivative of 8-azagona-12,17-dione occirs with simultaneous dehydrogenation of the C ring and leads to the 17-deoxo-9,11-dehydro, ehile desulfurization of the 1-dithioacetal of 8-aza-D-homogona-12,17-a-dione leads to the 12-deoxo derivative. By reaction of the 12-dithioacetal of 8-aza-D-homogona-17a-one with hydroxylamine, we obtained the 12-oximino derivative, which is the result of an unusual reaction at the site of the spiro coupling of the dithiolane ring with the 8-azasteroid ring.

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Authors
  1. O. V. Gulyakevich
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  2. A. L. Mikhal'chuk
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  3. A. A. Akhrem
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Additional information

Institute of Bioorganic Chemistry, Academy of Sciences of Belarus, Minsk, 220141. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 187–194, February, 1995. Original article submitted December 15, 1994.

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Gulyakevich, O.V., Mikhal'chuk, A.L. & Akhrem, A.A. Synthesis and properties of dithioacetals of conformationally constrainedα-acyl-β-aminovinyl ketones of the 8-azasteroid. Chem Heterocycl Compd 31, 160–166 (1995). https://doi.org/10.1007/BF01169673

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