Abstract
Tri- and tetraalkylammonium, 1,3-dialkylimidazolium, and 1,2,3-trialkylimidazolium salts with BF −4 , PF −6 , AlCl −4 , and Al2Cl −7 as counterions catalyze the Biginelli reaction, ensuring preparation of various 3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidine-2(1H)-thione derivatives in high yields in the absence of a solvent.
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REFERENCES
Atwal, K.S., Swanaon, B.N., Unger, S.E., Floyd, D.M., Moreland, S., Hedberg, A., and O’Reilly, B.S., J. Med. Chem., 1991, vol. 34, p. 806; Rovnyak, G.C., Atwal, K.S., Hedberg, A., Kimball, S.D., Moreland, S., Goudoutas, J.Z., O’Reilly, B.S., Schwartz, J., and Malley, M.F., J. Med. Chem., 1992, vol. 35, p. 3254; Grover, G.J., Dzwonzyk, S., McMullen, D.M., Normandin, D.E., Parham, C.S., Sleph, P.G., and Moreland, S., J. Cardiovasc. Pharmacol., 1995, vol. 26, p. 289.
Mayer, T.U., Kapoor, T.M., Haggarty, S.J., King, R.W., Schreiber, S.L., and Mitchison, T.J., Science, 1999, vol. 286, p. 971; Haggarty, S.J., Mayer, T.U., Miyamoto, D.T., Fathi, R., King, R.W., Mitchison, T.J., and Schreiber, S.L., Chem. Biol., 2000, vol. 7, p. 275.
Barrow, J.C., Nantermet, P.G., Selnick, H.G., Glass, K.L., Rittle, K.E., Gilbert, K.F., Steele, T.G., Homnick, C.F., Freidinger, R.M., Ransom, R.W., Kling, P., Reiss, D., Broten, T.P., Schorn, T.W., Chang, R.S., O’Malley, S.S., Olah, T.V., Ellis, J.D., Barrish, A., Kassahun, K., Leppert, P., Nagarathnam, D., and Forray, C., J. Med. Chem., 2000, vol. 43, p. 2703.
Heys, L., Moore, C.G., and Murphy, P.J., Chem. Soc. Rev., 2000, vol. 29, p. 57.
Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.
Kappe, C.O., Acc. Chem. Res., 2000, vol. 33, p. 879.
Hu, E.H., Sidler, D.R., and Dolling, U.-H., J. Org. Chem., 1998, vol. 63, p. 3454; Ma, Y., Qian, C., Wang, L., and Yang, M., J. Org. Chem., 2000, vol. 65, p. 3864; Lu, J., Bai, Y., Wang, Z., Yang, B., and Ma, Y., Tetrahedron Lett., 2000, vol. 41, p. 9075; Ranu, B.C., Hajra, A., and Jana, U., J. Org. Chem., 2000, vol. 65, p. 6270.
Peng, J. and Deng, Y., Tetrahedron Lett., 2001, vol. 42, p. 5917.
Itoh, H., Kato, I., Unoura, K., and Senda, Y., Bull. Chem. Soc. Jpn., 2001, vol. 74, p. 339.
Trost, B.M. and Kulawiec, R.J., J. Am. Chem. Soc., 1993, vol. 115, p. 2027; Backwall, J.-E. and Andreasson, U., Tetrahedron Lett., 1993, vol. 34, p. 5459.
Trost, B.M. and Rhee, Y.H., J. Am. Chem. Soc., 2002, vol. 124, p. 2528; Szumma, A. and Jurczak, J., Helv. Chim. Acta, 2001, vol. 84, p. 3760.
Karataev, A.M., Malovichko, N.S., Kovalevskaya, L.I., Elagina, S.K., and Moshchinskaya, N.K., Vopr. Khim. Khim. Tekhnol., 1974, vol. 33, p. 26.
Moshchinskaya, N.K. and Kovalevskaya, L.I., USSR Inventor’s Certificate no. 547 440, 1977; Chem. Abstr., 1977, vol. 87, no. 40 049.
Ionic Liquids in Synthesis, Wasserscheid, P. and Welton, T., Eds., Weinheim: Wiley, 2003.
Qian, C., Tian, H., and Ma, Y., Synth. Commun., 2003, vol. 33, p. 1459.
Mitra, A.K. and Banerjee, K., Synlett, 2003, no. 10, p. 1509.
Hu, E.H., Sidler, D.R., and Dolling U.-H., J. Org. Chem., 1998, vol. 63, p. 3454.
Yarim, M., Sarac, S., Ertan, M., Kilic, F.S., and Erol, K., Arzneim. Forsch., 2002, vol. 52, p. 27.
Xu, H. and Wang, Y.-G., J. Chem. Res., Synop., 2003, no. 6, p. 377.
Chun, S., Dzyuba, S.V., and Bartsch, R.A., Anal. Chem., 2001, vol. 73, p. 3737.
Suarez, P.A.Z., Dullius, J.E.L., Einloft, S., De Soura, R.F., and Dupont, J., Polyhedron, 1996, vol. 15, p. 1217.
Csihary, S., Fischmeisyer, C., Brunou, C., Horvath, I.T., and Dixneuf, P.H., New J. Chem., 2002, vol. 26, p. 1667.
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 524–528.
Original Russian Text Copyright © 2005 by Putilova, Kryshtal’, Zhdankina, Troitskii, Zlotin.
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Putilova, E.S., Kryshtal’, G.V., Zhdankina, G.M. et al. Alkylammonium and Alkylimidazolium Perhaloborates, Phosphates, and Aluminates as Catalysts in the Biginelli Reaction. Russ J Org Chem 41, 512–516 (2005). https://doi.org/10.1007/s11178-005-0196-9
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DOI: https://doi.org/10.1007/s11178-005-0196-9