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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*

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Akademika V. F. Kuprevicha St., Minsk, 220141, Republic of Belarus

    F. S. Pashkovsky, J. S. Dontsu, D. B. Rubinov & F. A. Lakhvich

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  1. F. S. Pashkovsky
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  2. J. S. Dontsu
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  3. D. B. Rubinov
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  4. F. A. Lakhvich
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Correspondence to F. S. Pashkovsky.

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*Dedicated to Academician G. Duburs on the occasion of his 80th birthday.

Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1545-1556, October, 2014.

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Pashkovsky, F.S., Dontsu, J.S., Rubinov, D.B. et al. 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*. Chem Heterocycl Comp 50, 1421–1431 (2015). https://doi.org/10.1007/s10593-014-1606-0

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