THE ROLE OF RETRO-MICHAEL REACTION IN THE SYNTHESIS OF 5-CARBAMOYL-2-PYRIDONES BY REACTION OF DIALKYL ETHOXYMETHYLIDENEMALONATES WITH ACETOACETAMIDES

Authors

  • Саргис C. Айоцян 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
  • Ани Г. Асратян 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
  • Ануш Х. Хачатрян 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
  • Алик Э. Бадасян 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
  • Светлана Г. Конькова 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
  • Генрих А. Паносян 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
  • Мушег С. Саргсян 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

DOI:

https://doi.org/10.1007/2481

Keywords:

amides of acetoacetic acid, ethoxymethylidenemalonates, 2-pyridone, retro-Michael reaction

Abstract

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.

How to Cite
Hayotsyan, S. S.; Hastratyan, A. H.; Khachatryan, A. Kh.; Badasyan, A. E.; Kon'kova, S. G.; Panosyan, H. A.; Sargsyan, M. S. Chem. Heterocycl. Compd. 2015, 51, 682. [Khim. Geterotsikl. Soedin. 2015, 51, 682.]

For this article in the English edition see DOI 10.1007/s10593-015-1757-7

Author Biographies

Саргис C. Айоцян, 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

Саргис С. Айоцян

Ани Г. Асратян, 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

Ани Г. Асратян

Ануш Х. Хачатрян, 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

Ануш Х. Хачатрян

Алик Э. Бадасян, 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

Алик Э. Бадасян

Светлана Г. Конькова, 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

Светлана Г. Конькова

Генрих А. Паносян, 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

Генрих А. Паносян

Мушег С. Саргсян, 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

Мушег С. Саргсян

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Published

2015-07-14

Issue

Vol. 51 No. 7 (2015)

Section

Original Papers