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REACTION OF NITROMETHANE WITH CINNAMOYL DERIVATIVES OF CYCLIC β-DICARBONYL COMPOUNDS. APPLICATION TO THE SYNTHESIS OF 2(3)-(4-ARYLPYRROLIDIN-2-YLIDENE)-1,3(2,4)-DIONES

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


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.

How to Cite
Pashkovsky, F. S.; Dontsu, J. S.; Rubinov, D. B.; Lakhvich, F. A. Chem. Heterocycl. Compd. 2015, 50, 1421. [Khim. Geterotsikl. Soedin. 2014, 1545.]

For this article in the English edition see DOI 10.1007/s10593-014-1606-0


Keywords


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

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