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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

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


Keywords


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

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