Email this article Synthesis of substituted dihydropyridines by reacting ethoxymethylidenemalonate with malonic acid N-arylamidoesters
- Authors: Hayotsyan S.S.1, Kon’kova S.G.1, Hasratyan A.G.1, Khachatryan A.K.1, Badasyan A.E.1, Sargsyan A.A.1, Panosyan G.A.1, Sargsyan M.S.1
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Affiliations:
- Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
- Issue: Vol 86, No 10 (2016)
- Pages: 2332-2337
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/216353
- DOI: https://doi.org/10.1134/S1070363216100145
- ID: 216353
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Abstract
Reactions of ethoxymethylidenemalonate with malonic acid N-arylamidoesters in the presence of triethylamine afforded diethyl 1-aryl-6-hydroxy-2-oxo-1,2-dihydropyridine-3,5-dicarboxylates via the cyclization of Michael adducts. In the presence of sodium ethoxide the formed adducts may be also involved into simultaneous retro-Michael reaction leading to the formation of ethyl 1-aryl-5-arylcarbamoyl-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylates. Direction of heterocyclization or retro-Michael reaction is determined by the acidity of the hydrogen atoms of adducts and basicity of catalyst.
About the authors
S. S. Hayotsyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Author for correspondence.
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
S. G. Kon’kova
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
A. G. Hasratyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
A. Kh. Khachatryan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
A. E. Badasyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
A. A. Sargsyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
G. A. Panosyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
M. S. Sargsyan
Institute of Organic Chemistry and Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: shayotsyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014
