Abstract
Reactions of 5-amino-3-(2-pyrrolyl)pyrazoles with β-dicarbonyl compounds (acetylacetone and ethyl acetoacetate) lead to formation of up to 90% of polysubstituted pyrazolo[1,5-a]pyrimidines.
Similar content being viewed by others
REFERENCES
Novinson, T., Dimmit, R.M.K., Simon, I.N., Robins, R.K., and O'Brien, D.E., J. Med. Chem., 1974, vol. 17, p. 645.
Springer, R.H., Scholten, M.B., O'Brien, D.E., Novinson, T., Miller, J.P., and Robins, R.K., J. Med. Chem., 1982, vol. 25, no. 3, p. 235.
Robins, R.K., Revankar, G.R., O'Brien, D.E., Springer, R.H., Novinson, T., Albert, A., Senga, K., Miller, I.P., and Streeter, D.G., J. Heterocycl. Chem., 1985, vol. 22, p. 601.
Huppatz, J.L., Aust. J. Chem., 1985, vol. 38, no. 1, p. 221.
Zaharan, M.A., El-Sharief, A.M.Sh., El-Gaby, M.S.A., Ammar, Y.A., and El-Said, U.H., Farmaco, 2001, vol. 56, no. 4, p. 277.
Auzzi, G., Bruni, F., Cecchi, L., Costanzo, A., and Vettori, L.P., J. Med. Chem., 1983, vol. 26, no. 12, p. 1706.
Senga, K., Novinson, T., Wilson, H.R., and Robins, R.K., J. Med. Chem., 1981, vol. 24, no. 5, p. 610.
Mustazza, C., Giudice, M.R., Borioni, A., and Gatta, F., J. Heterocycl. Chem., 2001, vol. 38, p. 1119.
Makarov, V.A., Anisimova, O.S., and Granik, V.G., Khim. Geterotsikl. Soedin., 1997, no. 3, p. 329; Emelina, E.E., Petrov, A.A., and Firsov, A.V., Russ. J. Org. Chem., 2001, vol. 37, p. 852; Makarov, V.A., Tafeenko, V.A., and Granik, V.G., Khim. Geterotsikl. Soedin., 1998, no. 12, p. 1676.
Makarov, V.A., Solov'eva, N.P., and Granik, V.G., Khim. Geterotsikl. Soedin., 1997, no. 5, p. 619.
Makarov, V.A., Solov'eva, N.P., Ryabova, O.B., and Granik, V.G., Khim. Geterotsikl. Soedin., 2000, no. 1, p. 73; Makarov, V.A., Solov'eva, N.P., Chernyshev, V.V., Sonnefeld, E., and Granik, V.G., Khim. Geterotsikl. Soedin., 2000, no. 1, p. 78.
Trofimov, B.A., Sobenina, L.N., Mikhaleva, A.I., Sergeeva, M.P., Sigalov, M.V., and Golovanova, N.I., Zh. Org. Khim., 1992, vol. 28, p. 1766.
Sobenina, L.N., Mikhaleva, A.I., Sergeeva, M.P., Petrova, O.V., Aksamentova, T.N., Kozyreva, O.V., Toryashinova, D.-S.D., and Trofimov, B.A., Tetrahedron, 1995, vol. 51, no. 14, p. 4223.
Trofimov, B.A., Abstracts of Papers, 1st Florida Heterocyclic Course and Conference, Gainesville, Florida: The University of Florida, 2000, F-1-F-18.
Demenev, A.P., Cand. Sci. (Chem.) Dissertation, Irkutsk, 2001.
Sobenina, L.N., Demenev, A.P., Mikhaleva, A.I., and Trofimov, B.A., Usp. Khim., 2002, vol. 71, no. 7, p. 641.
Sobenina, L.N., Mikhaleva, A.I., Petrova, O.V., Toryashinova, D.-S.D. Larina, L.I., Il'icheva, L.N., and Trofimov, B.A., Russ. J. Org. Chem., 1999, vol. 35, p. 1214.
Sobenina, L.N., Demenev, A.P., Mikhaleva, A.I., Petrova, O.V., Larina, L.I., Chernykh, G.P., Toriyashinova, D.-S.D., Vashchenko, A.V., and Trofimov, B.A., Sulfur Lett., 2000, vol. 24, no. 1, p. 1.
Danagulyan, G.G., Panakosyan, G.A., and Boyakhchyan, A.P., Khim. Geterotsikl. Soedin., 2002, no. 5, p. 665.
Bax, A. and Subramanian, S., J. Magn. Reson., 1986, vol. 67, no. 3, p. 565; Bax, A. and Summers, S., J. Am. Chem. Soc., 1986, vol. 108, no. 8, p. 2093.
Trofimov, B.A. and Mikhaleva, A.I., N-Vinilpirroly (N-Vinylpyrroles), Novosibirsk: Nauka, 1984, p. 262.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Petrova, O.V., Sobenina, L.N., Demenev, A.P. et al. Synthesis of Functionalized 2-(2-Pyrrolyl)pyrazolo[1,5-a]pyrimidines. Russian Journal of Organic Chemistry 39, 1471–1476 (2003). https://doi.org/10.1023/B:RUJO.0000010564.39518.5e
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000010564.39518.5e