Abstract
2-(4-Arylidene-3-methyl-5-oxo-4,5-dihydropyrazol-1-yl)-6-methylpyrimidin-4(3H)-ones were obtained by reaction of ethyl acetoacetate (6-methyl-4-oxo-3,4-dihydropyrimidin-2-yl)hydrazone with aromatic aldehydes. Successful cyclization occurs with aldehydes containing an auxochromic substituent in the para position.
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REFERENCES
US Patent 3 040 047, 1962, Chem. Abstr., 1963, vol. 58, P533e.
Jpn. Patent 7 443 985, 1974, Chem. Abstr., 1974, vol. 81, P49699w.
Naito, H., Sugimori, M., Mitsui, I., Nakamura, Y., Iwahawa, M., Ishii, M., Hirotani, K., Kumazawa, E., and Ejima, A., Chem. Pharm. Bull., 1999, vol. 47,no. 12, p. 1679.
Shvarts, G.Ya., Khim.-Farm. Zh., 1980, vol. 14,no. 9, p. 22.
Cristea, I., Stud. Univ. Babes-Bolyai, Chem., 1988, vol. 33,no. 2, p. 61.
Panea, I. and Cristea, I., Stud. Univ. Babes-Bolyai, Chem., 1996, vol. 41,no. 1, p. 9.
Libermann, D. and Rouaix, A., C. R. Acad. Sci., 1955, vol. 240,no. 9, p. 984.
Vanderhaeghe, H. and Claesen, M., Bull. Soc. Chim. Belg., 1959, vol. 68,no. 3, p. 30.
Brady, L.E. and Herbst, R.M., J. Org. Chem., 1959, vol. 24,no. 7, p. 922.
Baumbach, F., Henning, H.-G., and Hilgetag, G., Z. Chem., 1964, vol. 4,no. 2, p. 67.
Ivashchenko, A.V. and Garicheva, O.N., Khim. Geterotsikl. Soedin., 1982, no. 5, p. 579.
Baldea, I., Ghirisan, A., Silberg, I.A., and Cristea, I., Rev. Roum. Chim., 1997, vol. 42,no. 9, p. 767.
Simon, I.B. and Kovtunovskaya, I.I., Zh. Obshch. Khim., 1951, vol. 21,no. 4, p. 760.
Claesen, M. and Vanderhaeghe, H., Bull. Soc. Chim. Belg., 1959, vol. 68,no. 3, p. 47.
Cristea, I. and Farcasan, V., Rev. Chim., 1987, vol. 38,no. 8, p. 674.
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Erkin, A.V., Krutikov, V.I. & Chubraev, M.A. Synthesis of 2-(Pyrazol-1-yl)pyrimidine Derivatives by Cyclocondensation of Ethyl Acetoacetate (6-Methyl-4-oxo-3,4-dihydropyrimidin-2-yl)hydrazone with Aromatic Aldehydes. Russian Journal of General Chemistry 74, 423–427 (2004). https://doi.org/10.1023/B:RUGC.0000030401.30369.4d
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DOI: https://doi.org/10.1023/B:RUGC.0000030401.30369.4d