Skip to main content
SpringerLink
Log in

Alkylammonium and Alkylimidazolium Perhaloborates, Phosphates, and Aluminates as Catalysts in the Biginelli Reaction

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. 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.

    Article  CAS  PubMed  Google Scholar 

  2. 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.

    Article  CAS  PubMed  Google Scholar 

  3. 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.

    Article  CAS  PubMed  Google Scholar 

  4. Heys, L., Moore, C.G., and Murphy, P.J., Chem. Soc. Rev., 2000, vol. 29, p. 57.

    Article  CAS  Google Scholar 

  5. Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.

    Google Scholar 

  6. Kappe, C.O., Acc. Chem. Res., 2000, vol. 33, p. 879.

    Article  CAS  PubMed  Google Scholar 

  7. 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.

    Article  CAS  Google Scholar 

  8. Peng, J. and Deng, Y., Tetrahedron Lett., 2001, vol. 42, p. 5917.

    Article  CAS  Google Scholar 

  9. Itoh, H., Kato, I., Unoura, K., and Senda, Y., Bull. Chem. Soc. Jpn., 2001, vol. 74, p. 339.

    Article  CAS  Google Scholar 

  10. 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.

    Article  CAS  Google Scholar 

  11. 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.

    Article  CAS  PubMed  Google Scholar 

  12. 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.

    CAS  Google Scholar 

  13. Moshchinskaya, N.K. and Kovalevskaya, L.I., USSR Inventor’s Certificate no. 547 440, 1977; Chem. Abstr., 1977, vol. 87, no. 40 049.

  14. Ionic Liquids in Synthesis, Wasserscheid, P. and Welton, T., Eds., Weinheim: Wiley, 2003.

    Google Scholar 

  15. Qian, C., Tian, H., and Ma, Y., Synth. Commun., 2003, vol. 33, p. 1459.

    Article  Google Scholar 

  16. Mitra, A.K. and Banerjee, K., Synlett, 2003, no. 10, p. 1509.

  17. Hu, E.H., Sidler, D.R., and Dolling U.-H., J. Org. Chem., 1998, vol. 63, p. 3454.

    Article  CAS  Google Scholar 

  18. Yarim, M., Sarac, S., Ertan, M., Kilic, F.S., and Erol, K., Arzneim. Forsch., 2002, vol. 52, p. 27.

    CAS  Google Scholar 

  19. Xu, H. and Wang, Y.-G., J. Chem. Res., Synop., 2003, no. 6, p. 377.

  20. Chun, S., Dzyuba, S.V., and Bartsch, R.A., Anal. Chem., 2001, vol. 73, p. 3737.

    Article  CAS  PubMed  Google Scholar 

  21. Suarez, P.A.Z., Dullius, J.E.L., Einloft, S., De Soura, R.F., and Dupont, J., Polyhedron, 1996, vol. 15, p. 1217.

    Article  CAS  Google Scholar 

  22. Csihary, S., Fischmeisyer, C., Brunou, C., Horvath, I.T., and Dixneuf, P.H., New J. Chem., 2002, vol. 26, p. 1667.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Leninskii pr. 47, Moscow, 119991, Russia

    E. S. Putilova, G. V. Kryshtal’, G. M. Zhdankina, N. A. Troitskii & S. G. Zlotin

Authors
  1. E. S. Putilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. V. Kryshtal’
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. M. Zhdankina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. A. Troitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. G. Zlotin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 524–528.

Original Russian Text Copyright © 2005 by Putilova, Kryshtal’, Zhdankina, Troitskii, Zlotin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0196-9

Keywords

Search

Navigation