Abstract
The reaction of malononitrile dimer with phenyl isothiocyanate gave (6-amino-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ylidene)malononitrile which was then used as starting material in the synthesis of pharmacologically important fused pyrimidine derivatives, such as 4-dicyanomethylidene-1,5-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrrolo[2,3-d]pyrimidine, 6-cyano-4-dicyanomethylidene-7-methylsulfanyl-5-oxo-1-phenyl-2-thioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine, 6-dicyanomethylidene-3-phenyl-2-thioxo-1,2,3,6-tetrahydro-9H-purine, and 6-substituted 4-dicyanomethylidene-7-oxo-1-phenyl-2-thioxo-1,2,3,4,7,8-hexahydropteridines.
Similar content being viewed by others
References
Sharma, P., Rane, N., and Gurram, V.K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 4185.
Althaus, I.W., Chou, K.-C., Lemay, R.J., Franks, K.M., Deibel, M.R., Kezdy, F.J., Resnick, L., Busso, M.E., So, A.G., Downey, K.M., Romero, D.L., Thomas, R.C., Aristoff, P.A., Tarpley, W.G., and Reusser, F., Biochem. Pharmacol., 1996, vol. 51, p. 743.
Pandeya, S.N., Sriram, D., Nath, G., and De Clercq, E., Farmaco, 1999, vol. 54, p. 624.
Ghannoum, M.A., Abu, E.K., and El-Rayyes, N.R., Microbios, 1989, vol. 60, p. 23.
Wustrow, D., Akunne, H., Belliotti, T., Davis, M.D., Heffner, T., Kesten, S., Meltzer, L., Pugsley, T., and Wise, L., Eur. Neuropsychopharmacol., 1996, vol. 6, p. 4.
Balasankar, T. and Nagarajan, S., Heterocycl. Commun., 2004, vol. 10, p. 451.
Ferrero, M. and Gotor, V., Chem. Rev., 2000, vol. 100, p. 4319; Balzarini, J., Naesens, L., and De Clercq, E., Curr. Opin. Microbiol., 1998, vol. 1, p. 535.
Rahman, L.K.A. and Chhabra, S.R., Med. Res. Rev., 1988, vol. 8, p. 95; Grivsky, E.M., Lee, S., Sigel, C.W., Duch, D.S., and Nichol, C.A., J. Med. Chem., 1980, vol. 23, p. 327.
El-Desoky, S.I., Etman, H.A., Bondock, S.B., Fadda, A.A., and Metwally, M.A., Sulfur Lett., 2002, vol. 25, p. 199.
El-Desoky, S.I., Bondock, S.B., Etman, H.A., Fadda, A.A., and Metwally, M.A., Sulfur Lett., 2003, vol. 26, p. 127.
Mittelbach, M., Monatsh. Chem., 1985, vol. 116, p. 689.
Perrissin, M., Favre, M., Luu-Duc, C., Huguet, F., Gaultier, C., and Narcisse, G., Eur. J. Med. Chem., 1988, vol. 23, p. 453.
Cannito, A., Perrissin, M., Luu-Duc, C., Huguet, F., Gaultier, C., and Narcisse, G., Eur. J. Med. Chem., 1990, vol. 25, p. 635.
Vega, S., Alonso, J., Diaz, J.A., and Junquera, F., J. Heterocycl. Chem., 1990, vol. 27, p. 269.
Chakravarty, P.K., Greenlee, W.J., Kim, D., Mantlo, N.B., and Patchett, A.A., PCT Int. Patent Appl. WO 92-20 687, 1992; Chem. Abstr., 1993, vol. 118, no. 213 104d.
Shishoo, C.J. and Jain, K.S., J. Heterocycl. Chem., 1992, vol. 29, p. 883.
Senda, S. and Hirota, K., Chem. Pharm. Bull., 1974, vol. 22, p. 1459.
Huang, Z.T. and Shi, X., Synthesis, 1990, no. 2, p. 162.
Cain, C.K., Mallette, M.F., and Taylor, E.C., J. Am. Chem. Soc., 1946, vol. 68, p. 1996.
Honda, A. and Rogler, W., Eur. Patent no. 444 266, 1991; Chem. Abstr., 1991, vol. 115, no 232 284s.
Jacobson, K.A., van Galen, P.J.H., and Williams, M., J. Med. Chem., 1992, vol. 35, p. 407; Scammells, P.L., Baker, S.P., Belardinelli, L., and Olsson, R.A., J. Med. Chem., 1994, vol. 37, p. 2704; Mueller, C.E., Sauer, R., Geis, U., Frobenius, W., Talik, P., and Pawlowski, M., Arch. Pharm. Pharm. Med. Chem., 1997, vol. 330, p. 181.
Cottam, H.B., Shih, H., Tehrani, L.R., Wasson, D.B., and Carson, D.A., J. Med. Chem., 1996, vol. 39, p. 2.
Abou-Hadeed, K. and Pfleiderer, W., Pteridines, 1996, vol. 7, p. 113.
Tada, M., Asawa, Y., and Igarashi, M., J. Heterocycl. Chem., 1997, vol. 34, p. 973.
Author information
Authors and Affiliations
Additional information
Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 443–449.
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Abdel-Latif, E., Mustafa, H.M., Etman, H.A. et al. Synthesis of new purine, pteridine, and other pyrimidine derivatives. Russ J Org Chem 43, 443–448 (2007). https://doi.org/10.1134/S1070428007030219
Received:
Issue Date:
DOI: https://doi.org/10.1134/S1070428007030219