Skip to main content
Log in

1,1′-Butylenebis(3-methyl-3H-imidazol-1-ium) hydrogen sulfate as an efficient binuclear Brønsted ionic liquid for the synthesis of tacrine analogues

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

1,1′-Butylenebis(3-methyl-3H-imidazol-1-ium) hydrogen sulfate as an efficient, halogen-free, and reusable binuclear Brønsted ionic liquid catalyzed the synthesis of tacrine analogues. This method has the advantages of high yield, clean reaction, and simple methodology. The structure of the products was confirmed by IR, 1H NMR, 13C NMR, MS, and elemental analysis.

Graphical abstract

.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Shaw FH, Bentley G (1953) Aust J Exp Biol Med Sci 31:573

    Article  CAS  Google Scholar 

  2. Heilbronn E (1961) Acta Chem Scand 15:1386

    Article  CAS  Google Scholar 

  3. Maayani S, Weinstein H, Ben-Zvi N, Cohen S, Sokolovsky M (1974) Biochem Pharmacol 23:1263

    Article  CAS  Google Scholar 

  4. Summers WK, Majovski LV, Marsh GM, Tachiki K, Kling A (1986) N Engl J Med 315:1241

    Article  CAS  Google Scholar 

  5. Wurtman RJ (1985) Sci Am 252:48

    Article  Google Scholar 

  6. Altman HJ (ed) (1987) Alzheimer’s diseases problems prospects and perspectives. Plenum Press, New York

    Google Scholar 

  7. Francotte P, Graindorge E, Boverie S, de Tullio P, Pirotte B (2004) Curr Med Chem 11:1757

    Article  CAS  Google Scholar 

  8. Watkins PB, Zimmerman HJ, Knapp MJ, Gracon SI, Lewis KW (1994) J Am Med Assoc 271:992

    Article  CAS  Google Scholar 

  9. Ames DJ, Bhathal PS, Davies BM, Fraser JRE, Gibson PR, Roberts S (1990) N Z J Med 20:193

    Article  CAS  Google Scholar 

  10. Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M, Melchiorre C (2008) J Med Chem 51:347

    Article  CAS  Google Scholar 

  11. Harvey AL, Rowan EG (1988) Action of THA, 3,4-diaminopyridine, physostigmine and galanthamine on neuronal K+ currents at a cholinergic nerve terminal. In: Giacobini E, Becker R (eds) Current Research in Alzheimer Therapy. Taylor and Francis, New York

    Google Scholar 

  12. McKenna MT, Proctor GR, Young LC, Harvey AL (1997) J Med Chem 40:3516

    Article  CAS  Google Scholar 

  13. Drukarch B, Leysen JE, Stoof JC (1988) Life Sci 42:1011

    Article  CAS  Google Scholar 

  14. Sokhwinder J, Adem A, Winblad B, Oreland L (1992) Pharmacol Toxicol 71:213

    Article  Google Scholar 

  15. Kaul PN (1962) J Pharm Pharmacol 14:243

    Article  CAS  Google Scholar 

  16. Neilsen JA, Mena EE, Williams IH, Nocerine MR, Liston D (1988) Eur J Pharmacol 173:53

    Article  Google Scholar 

  17. McNally W, Roth M, Young R, Bockbrader H, Chang T (1989) Pharm Res 924

  18. Chaki H, Yamabe H, Sugano M, Morita S, Bessho T, Tabata R, Saito KI, Egawa M, Tobe A, Morinaka Y (1995) Bioorg Med Chem Lett 5:1495

    Article  CAS  Google Scholar 

  19. Thomae D, Kirsch G, Seck P (2007) Synthesis 1027

  20. Michalson ET, D’Andrea S, Freeman JP, Szmuszkovicz J (1999) Heterocycles 30:415

    Google Scholar 

  21. Marco JL, Rios C, Garcia AG, Villarroya M, Carreiras MC, Martins C, Eleutério A, Morreale A, Orozco M, Luque F (2004) Bioorg Med Chem 12:2199

    Article  CAS  Google Scholar 

  22. Barreiro EJ, Camara CA, Verli H, Brazil-Mas L, Castro NG, Cintra WM, Aracava Y, Fraga CAM (2003) J Med Chem 46:1144

    Article  CAS  Google Scholar 

  23. Shao D, Zou C, Luo C, Tang X, Li Y (2004) Bioorg Med Chem Lett 14:4639

    Article  CAS  Google Scholar 

  24. Alonso D, Dorronsoro I, Rubio L, Munõz P, García-Palomero E, Del Monte M, Bidon-Chanal A, Orozco M, Luque FJ, Castro A, Medina M, Martínez A (2005) Bioorg Med Chem 13:6588

    Article  CAS  Google Scholar 

  25. Camps P, Formosa X, Galdeano C, Gómez T, Munõz-Torrero D, Scarpellini M, Viayna E, Badia A, Clos MV, Camins A, Pallàs M, Bartolini M, Francesca Mancini F, Andrisano V, Estelrich J, Lizondo M, Bidon-Chanal A, Luque FJ (2008) J Med Chem 51:3588

    Article  CAS  Google Scholar 

  26. Yang L, Li J, Chai H, Lu H, Zhang Q, Shi D (2013) Chin J Chem 31:443

    Article  CAS  Google Scholar 

  27. Khaligh NG (2014) Chin J Catal 35:1036

    Article  CAS  Google Scholar 

  28. Khaligh NG (2014) Res Chem Intermed. doi:10.1007/s11164-014-1642-5

    Google Scholar 

  29. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, Davis JH Jr (2002) J Am Chem Soc 124:5962

    Article  CAS  Google Scholar 

  30. Arfan A, Bazureau JP (2005) Org Process Res Dev 9:743

    Article  CAS  Google Scholar 

  31. Wasserscheid P, Sesing M, Korth W (2002) Green Chem 4:134

    Article  CAS  Google Scholar 

  32. Seddon KR, Stark A, Torres MJ (2000) Pure Appl Chem 72:2275

    Article  CAS  Google Scholar 

  33. Fraga-Dubreuil J, Bourahla K, Rahmouni M, Bazureau JP, Hamelin J (2002) Catal Commun 3:185

    Article  CAS  Google Scholar 

  34. Gu Y, Zhang J, Duan Z, Deng Y (2005) Adv Synth Catal 347:512

    Article  CAS  Google Scholar 

  35. Kalita P, Kumar R (2012) Microporous Mesoporous Mater 149:1

    Article  CAS  Google Scholar 

  36. Khaligh NG (2014) Monatsh Chem 145:1643

    Article  CAS  Google Scholar 

  37. McKenna MT, Proctor GR, Young LC, Harvey AL (1997) J Med Chem 40:3516

    Article  CAS  Google Scholar 

  38. Da Costa JS, Pisoni DS, Da Silva CB, Petzhold CL, Russowsky D, Ceschi MA (2009) J Braz Chem Soc 20:1448

    Google Scholar 

  39. Yang D, Jiang K, Li J, Xu F (2007) Tetrahedron 63:7654

    Article  CAS  Google Scholar 

  40. Proctor GR, Harvey AL (2000) Curr Med Chem 7:295

    Article  CAS  Google Scholar 

  41. Hafelinger G, Steinmann L (1977) Angew Chem Int Ed 16:47

    Article  Google Scholar 

  42. OECD Chemical Group (1993) Ready biodegradability: modified OECD screening test. Method 301 E. OECD revised guidelines for tests for ready biodegradability, Paris

  43. Gathergood N, Garcia MT, Scammells PJ (2004) Green Chem 6:166

    Article  CAS  Google Scholar 

  44. Garcia MT, Gathergood N, Scammells PJ (2005) Green Chem 7:9

    Article  CAS  Google Scholar 

  45. APHA (American Public Health), AWWA (American Water Works Association), and WPCF (Water Pollution Control Federation) (1985) Method 508B, standard methods for the examination of water and wastewater, 16th edn. Washington, p 532

Download references

Acknowledgments

I am grateful to Research House of Professor Reza, Education Guilan for partial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nader Ghaffari Khaligh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1764 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ghaffari Khaligh, N. 1,1′-Butylenebis(3-methyl-3H-imidazol-1-ium) hydrogen sulfate as an efficient binuclear Brønsted ionic liquid for the synthesis of tacrine analogues . Monatsh Chem 146, 321–326 (2015). https://doi.org/10.1007/s00706-014-1325-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1325-3

Keywords

Navigation