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Synthesis of substituted dihydropyridines by reacting ethoxymethylidenemalonate with malonic acid N-arylamidoesters

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Abstract

Reactions of ethoxymethylidenemalonate with malonic acid N-arylamidoesters in the presence of triethylamine afforded diethyl 1-aryl-6-hydroxy-2-oxo-1,2-dihydropyridine-3,5-dicarboxylates via the cyclization of Michael adducts. In the presence of sodium ethoxide the formed adducts may be also involved into simultaneous retro-Michael reaction leading to the formation of ethyl 1-aryl-5-arylcarbamoyl-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylates. Direction of heterocyclization or retro-Michael reaction is determined by the acidity of the hydrogen atoms of adducts and basicity of catalyst.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    S. S. Hayotsyan, S. G. Kon’kova, A. G. Hasratyan, A. Kh. Khachatryan, A. E. Badasyan, A. A. Sargsyan, G. A. Panosyan & M. S. Sargsyan

Authors
  1. S. S. Hayotsyan
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  2. S. G. Kon’kova
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  3. A. G. Hasratyan
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  4. A. Kh. Khachatryan
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  5. A. E. Badasyan
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  6. A. A. Sargsyan
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  7. G. A. Panosyan
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  8. M. S. Sargsyan
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Corresponding author

Correspondence to S. S. Hayotsyan.

Additional information

Original Russian Text © S.S. Hayotsyan, S.G. Kon’kova, A.G. Hasratyan, A.Kh. Khachatryan, A.E. Badasyan, A.A. Sargsyan, G.A. Panosyan, M.S. Sargsyan, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 10, pp. 1685–1690.

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Hayotsyan, S.S., Kon’kova, S.G., Hasratyan, A.G. et al. Synthesis of substituted dihydropyridines by reacting ethoxymethylidenemalonate with malonic acid N-arylamidoesters. Russ J Gen Chem 86, 2332–2337 (2016). https://doi.org/10.1134/S1070363216100145

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  • DOI: https://doi.org/10.1134/S1070363216100145

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