Abstract
A procedure was proposed for the synthesis of 7-trifluoromethylazolo[1,5-a]pyrimidines by reactions of 2-ethoxyvinyl trifluoromethyl ketones and 2,2-diethoxyvinyl trifluoromethyl ketone with 5(3)-aminoazoles. The reactions occurred under mild conditions, and the products were formed with high yield and regioselectivity.
Similar content being viewed by others
References
Emelina, E.E., Petrov, A.A., and Selivanov, S.I., Russ. J. Org. Chem., 2008, vol. 44, p. 263.
Abu Almaati, T.M. and El-Taweel, F.M., J. Heterocycl. Chem., 2004, vol. 41, p. 109.
Almansa, C., de Arriba, A.F., Calvalcanti, F.L., Gomez, L.A., Miralles, A., Merlos, M., Garcia-Rafanell, J., and Forn, J., J. Med. Chem., 2001, vol. 44, p. 350.
Suzuki, M., Iwasaki, H., Fujikawa, Y., Sakashita, M., Kitahara, M., and Sakoda, R., Bioorg. Med. Chem. Lett. 2001, vol. 11, p. 1285; Hoepping, A., Diekers, M., Deuther-Conrad, W., Scheunemann, M., Fischer, S., Hiller, A., Wegner, F., Steinbach, J., and Brust, P., Bioorg. Med. Chem., 2008, vol. 16, p. 1184; Bharathi, Ch., Prabahar, K.J., Prasad, Ch.S., Kumar, M.S., Magesh, S., Handa, V.K., Dandala, R., and Naidu, A., J. Pharm. Biomed. Anal., 2007, vol. 44, p. 101.
George, C.F.P., Lancet, 2001, vol. 357, p. 1623.
Mirza, N.R., Rodgers, R.J., and Mathiasen, L.S., J. Pharmacol. Exp. Ther., 2006, vol. 316, p. 1291; Lippa, A., Czobor, P., Stark, J., Beer, B., Kostakis, E., Gravielle, M., Bandyopadhyay, S., Russek, S.J., Gibbs, T.T., Farb, D.H., and Skolnick, P., Proc. Natl. Acad. Sci. USA., 2005, vol. 102, p. 7380.
Hojo, M., Masuda, R., Kokuryo, Y., Shioda, H., and Matsuo, S., Chem. Lett., 1976, p. 499.
Hojo, M., Masuda, R., and Okada, E., Synthesis, 1986, p. 1013.
Hojo, M., Masuda, R., and Okada, E., Synthesis, 1989, p. 215.
Martins, M.A.P., Cunico, W., Scapin, E., Emmerich, D.J., Fiss, G.F., Rosa, F.A., Bonacorso, H.G., Zanatta, N., and Flores, A.F.C., Lett. Org. Chem., 2006, vol. 3, p. 358.
Takahashi, M., Nagaoka, H., and Inoue, J., J. Heterocycl. Chem., 2004, vol. 41, p. 525.
Fuller, R. and Kobayashi, Y., Biomedicinal Aspects of Fluorine Chemistry, Amsterdam: Elsevier, 1982.
Reiter, J., Pongó, L., and Kővesdi, I., J. Heterocycl. Chem., 1995, vol. 32, p. 407.
Baraldi, P.G., Fruttarolo, F., Tabrizi, M.A., Romagnoli, R., Preti, D., Ongani, E., El-Kasheh, H., Carrion, M.D., and Borea, P.A., J. Heterocycl. Chem., 2007, vol. 44, p. 355.
Chauhan, S.M.S. and Junjappa, H., Tetrahedron, 1976, vol. 12, p. 1779.
Auzzi, G., Bruni, F., Cecchi, L., Costanzo, A., Vettori, L.P., Pirisino, R., Corrias, M., Ignesti, G., Banchelli, G., and Raimondi, L., J. Med. Chem., 1983, vol. 26, p. 1706.
Emelina, E.E., Petrov, A.A., and Firsov, A.V., Russ. J. Org. Chem., 2001, vol. 37, p. 852.
Emelina, E.E., Petrov, A.A., and Firsov, A.V., Russ. J. Org. Chem., 2003, vol. 39, p. 277.
Emelina, E.E. and Petrov, A.A., Materialy I Mezhdunarodnoi konferentsii “Khimiya i biologicheskaya aktivnost’ azotistykh geterotsiklov i alkaloidov” (Proc. Ist Int. Conf. “Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids”), Moscow, 2001, vol. 2, p. 102.
Filimonov, D.A. and Poroikov, V.V., Ros. Khim. Zh., 2006, vol. 50, no. 2, p. 66.
Poroikov, V. and Filimonov, D., Predictive Toxicology, Helma, C., Ed., Boca Raton: Taylor & Francis, 2005, p. 459.
Leibscher, H., Hartmann, H., and Reuther, I., FRG Patent no. 145 750, 1981; Chem. Abstr., 1981, vol. 95, no. 80 952 m.
Grandberg, I.I., Din Vei-Py, and Kost, A.N., Zh. Obshch. Khim., 1961, vol. 31, p. 2311.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.E. Emelina, A.A. Petrov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 427–430.
For communication IV, see [1].
Rights and permissions
About this article
Cite this article
Emelina, E.E., Petrov, A.A. α-aminoazoles in the Synthesis of heterocycles: V. Synthesis of azolo[1,5-a]pyrimidines from 2-ethoxyvinyl trifluoromethyl ketones and 2,2-diethoxyvinyl trifluoromethyl ketone. Russ J Org Chem 45, 417–420 (2009). https://doi.org/10.1134/S1070428009030117
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428009030117