Abstract
Hantzch’s type reaction of methyl acetopyruvate(2a), methyl 3-aminocrotonate(3) and 3-nitrobenzaldehyde(4) led to dimethyl 3-acetyl-6-methyl-4-(3′-nitrophenyl)-2,5-dicarboxylate(5a) and methyl 2,6-dimethyl-5-(1′, 2′-dioxo-2′-methoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate(6a) in 26.7 and 9.2% yield, respectively. On the other hand, methyl 2,6-dimethyl-4-(3′-nitrophenyl)-1, 4-dihydropyridine 3-carboxylate(9) was acylated by ethyl oxaly chloride to give methyl 2,6-dimethyl-5-(1′,2′-dioxo-2′-ethoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate(6b) in 76.8% yield.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Grün, Von G. and Fleckenstein, A.: Die elektro mechanische Entkoppelung der glatten Gefä β muskulatur als Grundprinzip der Coronardilatation durch 4-(2′-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonsäure-dimethylester (BAY a 1040, Nifedipine).Arzneim. Forsch. (Drug. Res.),22, 334 (1972).
Bossert, F. and Vater, W.: Dihydropyridine, eine Gruppe stark wirksamer Coronartherapeutika.Naturwissenschaften,58, 578 (1971).
Meyer, Von H., Bossert, F., Wehinger, E., Stoepel, K. and Vater, W.: Synthese und Vergleichende pharmakolgische Untersuchungen von 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl) pyridine-3,5-dicarbonsäureestern mit nichtidentischen Esterfunktionen.Arzneim. Forsch. (Drug. Res.),31, 407 (1981).
Iwanami, M., Shibanuma, T., Fujiomoto, M., Kawai, R., Tamazawa, K., Takenaka, T., Takahashi, K. and Murakami, M.: Synthesis of New Water-soluble Dihydropyridine Vasodilators.Chem. Pharm. Bull. 27, 1426 (1979).
Prous, J., Blancafort, P., Castäner, J., Serradell, M.N. and Mealy, N.: Biologically Active 1, 4-Dihydropyridine Derivatives.Drugs of the Future,6, 427 (1981).
Bossert, F., Meyer, H. and Wehinger, E.: 4-Aryldihydropyridines, a New Class of Highly Active Calcium Atangonists.Angew. Chem. Int. Ed. Engl. 20, 762 (1981).
Stout, D.M. and Meyers, A.I.: Recent Advances in the Chemistry of Dihydropyridines.Chem. Rev. 82, 223 (1982).
Sausins, A. and Duburs, G.: Synthesis of 1, 4-Dihydropyridines by Cyclocondensation Reactions.Heterocycles,27, 269 (1988).
Hof, R.P. and Vuorela H.J.: Assessing Calcium Antagonism on Vascular Smooth Muscle: A Comparison of Three Methods.Pharmacol J. Methods,9, 41 (1983).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Suh, J., Hong, Y. Synthesis of methyl 2, 6-dimethyl-5-(1′, 2′-dioxo-2′-ethoxyethyl)-4-(3′-nitrophenyl)-1,4-dihydropyridine-3-carboxylate. Arch. Pharm. Res. 13, 257–260 (1990). https://doi.org/10.1007/BF02856531
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02856531