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Russian Journal of Organic Chemistry

, Volume 46, Issue 8, pp 1121–1134 | Cite as

Synthesis of chiral benzoacridinone derivatives by three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and cyclic β-diketones

  • S. S. Koval’skaya
  • N. G. Kozlov
  • E. A. Dikusar
Article

Abstract

Three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and cyclic β-diketones gave 7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12-hexahydro-7H-benzo[c]acridin-8-one derivatives possessing three or more asymmetric carbon atoms. Steric factors were found to be responsible for the predominant formation of the (7R)-isomers (R/S ≈ 7: 5) and orientation of substituents in the cyclohexenone fragment. The same factors determined complete regioselectivity of the reaction with methyl 2,4-dioxocyclohexane-1-carboxylates as dicarbonyl component, which led to exclusive formation of methyl 8-oxobenzoacridine-11-carboxylates. In the reaction of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and barbituric acid as dicarbonyl component, the only product was that formed by two-component condensation of barbituric acid with bicyclic aldehyde.

Keywords

Barbituric Acid Hexahydro Bornane Dimethyl Malonate Methoxycarbonyl Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • S. S. Koval’skaya
    • 1
  • N. G. Kozlov
    • 1
  • E. A. Dikusar
    • 1
  1. 1.Institute of Physical Organic ChemistryNational Academy of Sciences of BelarusMinskBelarus

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