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Synthesis of substituted 1,2-dihydropyridines by reaction of ethyl N-arylmalonamates with ethyl 2-(ethoxymethylidene)-3-oxobutanoate

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Abstract

Michael addition of ethyl N-arylmalonamates to ethyl 2-(ethoxymethylidene)-3-oxobutanoate in ethanol in the presence of triethylamine at room temperature afforded the corresponding adducts which underwent cyclization to diethyl 1-aryl-6-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarboxylates in 17–65% yield. N-Alkylmalonamic acid esters failed to react with ethyl 2-(ethoxymethylidene)-3-oxobutanoate under analogous conditions.

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Authors and Affiliations

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

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

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  1. S. S. Hayotsyan
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  2. A. H. Hasratyan
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  3. A. A. Sargsyan
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  4. A. Kh. Khachatryan
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  5. A. E. Badasyan
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  6. S. G. Kon’kova
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  7. M. S. Sargsyan
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Correspondence to S. S. Hayotsyan.

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Original Russian Text © S.S. Hayotsyan, A.H. Hasratyan, A.A. Sargsyan, A.Kh. Khachatryan, A.E. Badasyan, S.G. Kon’kova, M.S. Sargsyan, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 6, pp. 871–875.

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Hayotsyan, S.S., Hasratyan, A.H., Sargsyan, A.A. et al. Synthesis of substituted 1,2-dihydropyridines by reaction of ethyl N-arylmalonamates with ethyl 2-(ethoxymethylidene)-3-oxobutanoate. Russ J Org Chem 52, 857–861 (2016). https://doi.org/10.1134/S1070428016060166

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  • DOI: https://doi.org/10.1134/S1070428016060166

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