Abstract
The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-[(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1-[(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by 1H NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity.
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REFERENCES
Fedorova, E.V., Meshcheryakov, M.P., Ganina, M.B., Moskvin, A.V., and Ivin, B.A., Zh. Obshch. Khim., 2004, vol. 74,no. 1, p. 139.
Moskvin, A.V., Platonov, V.G., Il'enko, V.I., and Ivin, B.A., Abstracts of Papers, Simpozium “Novye podkhody k tselenapravlennomu konstruirovaniyu protivovirusnyh preparatov” (Symp. “New Approaches to Design of Antiviral Preparations”), St. Petersburg, 1994, p. 6.
Kul'pina, G.V., Cand. Sci. (Chem.) Dissertation, Leningrad, 1990.
Levine, H., Brody, R., and Westheinler, F., J. Biochem., 1980, vol. 19,no. 22, p. 4993.
De Clercq, E., Clin. Microbiol. Rev., 1997, vol. 10,no. 4, p. 674.
Kraevsky, A.A. and Watanabe, K.A., Bioinform. M., 1993.
Moskvin, A.V., Ksenofontova, G.V., Studentsov, E.P., and Ivin, B.A., Zh. Obshch. Khim., 1994, vol. 64,no. 3, p. 492.
Moskvin, A.V., Ksenofontova, G.V., Studentsov, E.P., and Ivin, B.A., Zh. Obshch. Khim., 1994, vol. 64,no. 3, p. 485.
Bojarski, J.T., Mokrocz, J.L., and Barton, H.J., Adv. Heterocycl. Chem., 1987, vol. 38, p. 229.
Zoorob, H.H., Abou-El Zahab, M.M., Abdel-Mogib, M., and Ismail, M.A., Tetrahedron, 1996, vol. 52,no. 30, p. 10147.
Figueroa-Villar, J.D. and Cruz, E.R., Tetrahedron, 1993, vol. 49,no. 14, p. 2855.
Ahluwalia, V.K., Sharma, M.K., Aggarwal, R., Chauchan, A., and Sharma, R., Indian J. Chem., Sect. B, 1991, vol. 30,no. 6, p. 598.
King, F.E., King, T.J., and Thompson, G.B., J. Chem. Soc., 1948, no. 4, p. 552.
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Studentsov, E.P., Kokhanovskii, A.N., Ganina, M.B. et al. Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N1-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives. Russian Journal of General Chemistry 74, 261–265 (2004). https://doi.org/10.1023/B:RUGC.0000025513.88248.94
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DOI: https://doi.org/10.1023/B:RUGC.0000025513.88248.94