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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

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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.

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References

  1. Emelina, E.E., Petrov, A.A., and Selivanov, S.I., Russ. J. Org. Chem., 2008, vol. 44, p. 263.

    Google Scholar 

  2. Abu Almaati, T.M. and El-Taweel, F.M., J. Heterocycl. Chem., 2004, vol. 41, p. 109.

    Article  Google Scholar 

  3. 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.

    Article  CAS  Google Scholar 

  4. 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.

    Article  CAS  Google Scholar 

  5. George, C.F.P., Lancet, 2001, vol. 357, p. 1623.

    Article  Google Scholar 

  6. 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.

    Article  CAS  Google Scholar 

  7. Hojo, M., Masuda, R., Kokuryo, Y., Shioda, H., and Matsuo, S., Chem. Lett., 1976, p. 499.

  8. Hojo, M., Masuda, R., and Okada, E., Synthesis, 1986, p. 1013.

  9. Hojo, M., Masuda, R., and Okada, E., Synthesis, 1989, p. 215.

  10. 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.

    Article  CAS  Google Scholar 

  11. Takahashi, M., Nagaoka, H., and Inoue, J., J. Heterocycl. Chem., 2004, vol. 41, p. 525.

    Article  CAS  Google Scholar 

  12. Fuller, R. and Kobayashi, Y., Biomedicinal Aspects of Fluorine Chemistry, Amsterdam: Elsevier, 1982.

    Google Scholar 

  13. Reiter, J., Pongó, L., and Kővesdi, I., J. Heterocycl. Chem., 1995, vol. 32, p. 407.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. Chauhan, S.M.S. and Junjappa, H., Tetrahedron, 1976, vol. 12, p. 1779.

    Article  Google Scholar 

  16. 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.

    Article  CAS  Google Scholar 

  17. Emelina, E.E., Petrov, A.A., and Firsov, A.V., Russ. J. Org. Chem., 2001, vol. 37, p. 852.

    Article  CAS  Google Scholar 

  18. Emelina, E.E., Petrov, A.A., and Firsov, A.V., Russ. J. Org. Chem., 2003, vol. 39, p. 277.

    Article  CAS  Google Scholar 

  19. 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.

    Google Scholar 

  20. Filimonov, D.A. and Poroikov, V.V., Ros. Khim. Zh., 2006, vol. 50, no. 2, p. 66.

    CAS  Google Scholar 

  21. Poroikov, V. and Filimonov, D., Predictive Toxicology, Helma, C., Ed., Boca Raton: Taylor & Francis, 2005, p. 459.

    Google Scholar 

  22. http://www.ibmc.msk.ru/PASS .

  23. Leibscher, H., Hartmann, H., and Reuther, I., FRG Patent no. 145 750, 1981; Chem. Abstr., 1981, vol. 95, no. 80 952 m.

  24. Grandberg, I.I., Din Vei-Py, and Kost, A.N., Zh. Obshch. Khim., 1961, vol. 31, p. 2311.

    CAS  Google Scholar 

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Correspondence to E. E. Emelina.

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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].

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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

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  • DOI: https://doi.org/10.1134/S1070428009030117

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