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

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...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-07, Vol.51 (7), p.682-687
Main Authors: Hayotsyan, Sargis S., Hastratyan, Ani H., Khachatryan, Anush Kh, Badasyan, Alik E., Końkova, Svetlana G., Panosyan, Henry A., Sargsyan, Mushegh S.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Hydrogen
Organic Chemistry
Pharmacy
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-015-1757-7