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The role of retro-Michael reaction in the synthesis of 5-carbamoyl-2-pyridones by reaction of dialkyl ethoxymethylidenemalonates with acetoacetamides

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of dialkyl ethoxymethylidenemalonates with arylamides of acetoacetic acid was studied for the purpose of creating a new method for the synthesis of substituted 2-pyridones containing a carbamoyl group. This reaction was shown to occur in the presence of triethylamine in ethanol solution at room temperature, forming mainly retro-Michael products, N,1-diaryl-5-acetyl-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxamides. Simultaneously, depending on the molar ratio of reagents, triethylammonium 5-acetyl-3-alkoxycarbonyl-1-aryl-6-oxo-1,6-dihydropyridin-2-olates were also formed at the same time. The results of this reaction can be explained by the different acidity of the acidic hydrogen atoms in Michael adduct.

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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 the Republic of Armenia, 26 Azatutyan Ave., Yerevan, 0014, Armenia

    Sargis S. Hayotsyan, Ani H. Hastratyan, Anush Kh. Khachatryan, Alik E. Badasyan, Svetlana G. Końkova & Mushegh S. Sargsyan

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

    Henry A. Panosyan

Authors
  1. Sargis S. Hayotsyan
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  2. Ani H. Hastratyan
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  3. Anush Kh. Khachatryan
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  4. Alik E. Badasyan
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  5. Svetlana G. Końkova
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  6. Henry A. Panosyan
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  7. Mushegh S. Sargsyan
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Correspondence to Sargis S. Hayotsyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(7), 682–687

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Hayotsyan, S.S., Hastratyan, A.H., Khachatryan, A.K. et al. The role of retro-Michael reaction in the synthesis of 5-carbamoyl-2-pyridones by reaction of dialkyl ethoxymethylidenemalonates with acetoacetamides. Chem Heterocycl Comp 51, 682–687 (2015). https://doi.org/10.1007/s10593-015-1757-7

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  • DOI: https://doi.org/10.1007/s10593-015-1757-7

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