Polyfunctional imidazoles: II. Synthesis and reactions with nucleophilic reagents of 1-substituted 2,4-dichloro-1H-imidazole-5-carbaldehydes
Tóm tắt
1-Alkyl(aryl)imidazolidine-2,4-diones reacted with Vilsmeier-Haack reagent affording 1-alkyl(aryl)-2,4-dichloro-1H-imidazole-5-carbaldehydes whose reactions with sodium azide, sodium alkoholates, with phenols, thiols, and secondary cycloalkylamines led to the substitution of chlorine in the position 2 of the imidazole ring. The reaction with primary amines resulted in the condensation products at the aldehyde group.
Tài liệu tham khảo
Chornous, V.A., Bratenko, M.K., and Vovk, M.V., Zh. Org. Khim., 2009, vol. 45, p. 1219.
Chien, T-Ch., Saluya, S.S., Drach, D.C., and Towsend, L.B., J. Med. Chem., 2004, vol. 47, p. 5443.
Tomioka, H., Yano, T., Takada, X., Takeda, H., and Hirata, N., Agricul. Biol. Chem., 1991, vol. 55, p. 1601.
Almansa, C., Alfon, J., de, Arrida, A.F., Cavalcanti, F.L., Escamilla, J., Gomes, L.A., Miralles, A., Soliva, R., Bartroli, J., Carseller, E., Merlos, M., and Garcia-Bofanell, J., J. Med. Chem., 2003, vol. 46, p. 3463.
Byuttel’mann, B., Chekarelli, S.M., Ieshke, G., Porter, R. Kh.F., Fiaira, E., Kol’chevski, Z., EA Patent 010577, vol. 1, 2008; http: www.eapo.org/rus/bulletin/ea200805/HTML/010577.html.
Mjalli, A., Europe Inventor’s Certificate 2082740A2, 2009; http://ep.espacenet.com
Sugimoto, H. and Fujiwara, T., US Patent 6147097, 2000; http://patft.uspto.gov/
Dumeunier, R., Lamberth, C., Trah, S., and Wendeborn, S., WO Inventor’s Certidicate 053102, 2009; http://ep.espacenet.com/
Dumeunier, R., Lamberth, C., and Trah, S., WO Inventor’s Certidicate 127615, 2009; http://ep.espacenet.com/
Albuquerque, J.F.C., Rolea, Filho, J.A., Brandao, S.S.T., Lima, M.C.A., Ximenes, E.A., Galdino, S.L., Pitta, I.R., Chantegrel, J., Perrisin, M., and Luu-Duc, C., Farmaco, 1999, vol. 54, p. 77.
Kochkanyan, V.O., Israelyan, Yu.A., and Zaritovskii, A.I., Khim. Geterotsikl. Soedin., 1978, p. 87.
Beckurts, Y., Frerich, G., and Beckurts, H., Arch. Pharm., 1899, vol. 237, p. 331.
Baranov, S.I., Kochkanyan, R.O., Zaritovskii, A.I., Belova, G.I., and Radnova, S.S., Khim. Geterotsikl. Soedin., 1975, p. 85.
Iddon, B. and Khan, N., Tetrahedron Lett., 1986, vol. 27, p. 1635.
Eriksen, B.L., Vedso, P., and Begtrup, M., J. Org. Chem., 2001, vol. 66, p. 8344.
Chemical Reactivity and Reaction Paths, Klopman, G., Ed., New York: Wiley, 1974.
Gaussian 98W (Revision, A.7), Pittsburgh: Gaussian, Inc., 1998. www.gaussian.com/
Foster, J.P. and Weinhold, F., J. Am. Chem. Soc., 1980, vol. 102, p. 7211.
Besler, B.H., Merz, K.M., and Kollman, P.A., J. Comp. Chem., 1989, vol. 11, p. 431.
Singh, U.C. and Kollman, P.A., J. Comp. Chem., 1984, vol. 5, p. 129.
Sykes, P., A Guidebook to Mechanism in Organic Chemistry, 2nd edn., London: Longmans, 1966.
Sheldrikc, G.M., SHELXS97. Program for Solution of Crystal Structure, University of Gtsttingen, Germany, 1997.
Sheldrik, G.M., SHELXS97. Program for the Refinement of Crystal Structures, Univetsity of Gtsttingen, Germany, 1997.