Abstract
Hantzsch synthesis of 5-formyluracil (1), methyl acetoacetate (2) and methyl 3-aminocrotonate (3) gave 2,6-dimethyl-4-(2,4-dioxo-5-pyrimidyl)-1, 4-dihydropyridine-3, 5-dicarboxylic acid dimethylester (4a) in 54.6% yield. As the same procedure, 1,3-dimethyl-5-formyl-uracil (6) gave 2,6-dimethyl-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidyl)-1, 4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (7a) in 52.2% yield.4a was methylated to afford7a also in 52% yield.
Similar content being viewed by others
Literature Cited
Grun, Von G. and Fleckenstein, A.: Die elektromechanische Entkoppelung der glatten Gafa β-muskulatur als Grund-prinzip der Coronardilatation durch 4-(2-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5 di-carbonsaure-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. und Vater, W.: Synthese und Vergleichende pharmakoligische Untersuchungen von 1, 4-Dihydro-2,6-dimethyl-4-(3-nitro phenyl)pyridine-3,5-dicarbonsäure estern mit nichtidentischen Esterfunktione.Arzneim. Forsch. (Drug Res.),31, 407 (1981).
Iwanami M., Shibanuma, T., Fujimoto, 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., Castaner, 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 Antagonists.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).
Prous, J.R.: Isradipine.Drugs of the Future,10, 747 (1985).
Prous, J.R.: 140–931.Annual Drug Data Report,10, 642 (1988).
Mekenna, J.L., Schlicksupp, L., Natale, N.R., Willett, R.D., Maryanoff, B.E., and Flaim, S.F.: Cardioactivity and Solidstate Structure of Two 4-Isoxazolyldihydropyridines Related to the 4-Aryldihydropyridine Calcium-Channel Blockers.J. Med. Chem.,31, 473 (1988).
Itahara, T., Fujii, Y. and Tada, M.: Oxidation of Thymines by Peroxosulfate Ions in Water.J. Org. Chem.,53, 3421 (1988).
Ressner, E.C., Kampt, A., Mertes, M.P. In Nucleic Acid Chem., Townsend, L.B. and Tipson, R.S., Eds. Wiley: New York, p. 89 (1978).
Brossmer, R. und Ziegler, D.: Zur Darstellung Heterocyclischer Aldehyde.Tetrahedron Letters,43, 5253 (1966).
Abdulla, R.F. and Brinkmeyer, R.S.: The Chemistry of Formamide Acetals.Tetrahedron,35, 1675 (1979).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Suh, J., Hong, Y. & Bae, M. Synthesis of 4-(2,4-dioxo-5-pyrimidyl)-1,4-dihydropyridine derivatives. Arch. Pharm. Res. 13, 310–313 (1990). https://doi.org/10.1007/BF02858164
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02858164