Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1421–1431 | Cite as

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*

  • F. S. Pashkovsky
  • J. S. Dontsu
  • D. B. Rubinov
  • F. A. Lakhvich

We have shown that reaction of nitromethane with cinnamoyl derivatives of five- and six-membered carbo- and heterocylic β-dicarbonyl compounds in the presence of 1,1,3,3-tetramethylguanidine proceeds according to the mechanism of 1,4-conjugate addition to the enone fragment of cinnamoyl moiety to give 2(3)-( 3-aryl-4-nitrobutanoyl)-substituted cyclic 1,3- or 2,4-diones in good to excellent yields. Chemoselective reduction of nitro function of the latter leads to synthetically useful and biologically interesting 2(3)-(4-arylpyrrolidin-2-ylidene) derivatives.


2(3)-(4-arylpyrrolidin-2-ylidene)-1,3(2,4)-diones cyclic β-tricarbonyl compounds enones nitromethane chemoselectivity Michael addition reduction 


The authors thank the Belorussian Foundation for Basic Research (grant X12P-083) for financial support.


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • F. S. Pashkovsky
    • 1
  • J. S. Dontsu
    • 1
  • D. B. Rubinov
    • 1
  • F. A. Lakhvich
    • 1
  1. 1.Institute of Bioorganic ChemistryNational Academy of Sciences of BelarusMinskRepublic of Belarus

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