Chemistry of Heterocyclic Compounds

, Volume 29, Issue 3, pp 313–320 | Cite as

Structure and properties of 8-azasteroids synthesized by regio- and stereoselective annelation of 3,4-dihydroisoquinolines by asymmetric 2-acyl-1,3-cyclohexanediones

  • A. L. Mikhal'chuk
  • O. V. Gulyakevich
  • D. B. Rubinov
  • A. A. Akhrem


It was found that annelation of 3,4-dihydroisoquinolines by 2-acyl-1,3-cyclohexanediones takes place regio- and stereoselectively, leading to C(11)- and C(17)-substituted derivatives of the 8-aza-D-homogonane series with a trans-disposition of the substituents (Me, Br, Cl, COOMe) at the above positions relative to the angular substituent (H, Me) at C(9). It was shown that the C(17)-halogen and methoxycarbonyl derivatives exist in crystals in the form of one stereoisomer, while in solutions as a mixture of stereoisomers, caused by a keto-enol tautomerism of the C(17a)-carbonyl. In solutions of acids, these derivatives exist in N(8)- ... — C(17a) immonium-enol form, as one stereoisomer. It was found that the C(11)-methyl derivatives are obtained in the form of two restrained conformers with respect to ring C, which on boiling are reduced to one conformer. The assignment of the enol regiomers of 4-substituted 2-acetyldimedones has been carried out.


Methyl Organic Chemistry Carbonyl Cyclohexanediones Halogen 
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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • A. L. Mikhal'chuk
    • 1
  • O. V. Gulyakevich
    • 1
  • D. B. Rubinov
    • 1
  • A. A. Akhrem
    • 1
  1. 1.Institute of Bioorganic ChemistryAcademy of Sciences of BelarusMinsk

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