Skip to main content

Advertisement

SpringerLink
Log in

Novel SO3H-Functionalized Ionic Liquids Based on Benzimidazolium Cation: Efficient and Recyclable Catalysts for One-Pot Synthesis of Biscoumarin Derivatives

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

In this article, a new group of SO3H-functionalized ionic liquids based on benzimidazolium cation was synthesized and used as environmentally benign catalysts for the one-pot synthesis of biscoumarin derivatives. The ionic liquids showed high catalytic activities and reusabilities with good to excellent yields of the desired products. H 0 (Hammett function) values and the minimum-energy geometries of SO3H-functionalized ionic liquids were determined and the results revealed that the acidities and catalytic activities of ionic liquids in the synthesis of biscoumarin derivatives were related to their structures.

Graphical Abstract

The simple, more efficient way for synthesis of biscoumarin derivatives has been developed. This new method abandon the traditional hazardous organic liquid and is carried out by using a one-pot reaction of 4-hydroxycoumarin with aromatic aldehydes in the presence of novel SO3H-functionalized ionic liquids based on benzimidazolium cation as catalysts. The ionic liquids showed high catalytic activities and reusabilities with good to excellent yields of the desired products. H 0 (Hammett function) values and the minimum-energy geometries of SO3H-functionalized ionic liquids were determined and the results revealed that the acidities and catalytic activities of ionic liquids in the synthesis of biscoumarin derivatives were influenced by their structures.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Hinman JW, Hoeksema H, Caron EL, Jackson WG (1956) J Am Chem Soc 78:1072

    Article  CAS  Google Scholar 

  2. Manolov L, Raleva S, Genova P, Savov A, Froloshka L, Dundarova D, Argirova R (2006) Bioinorg Chem Appl: 1

  3. Manolov I, Maichle-Moessmer C, Nicolova I, Danchev N (2006) Arch Pharm (Weinheim) 339:319

    Article  CAS  Google Scholar 

  4. Khan KM, Iqbal S, Lodhi MA, Maharvi GM, Ullah Z, Choudhary MI, Rahman AU, Perveen S (2004) Bioorg Med Chem 12:1963

    Article  CAS  Google Scholar 

  5. Brufola G, Fringuelli F, Piermatti O, Pizzo F (1996) Heterocycles 43:1257

    Article  CAS  Google Scholar 

  6. Yadav JS, Reddy BVS, Basak AK, Visali B, Narsaiah AV, Nagaiah K (2004) Eur J Org Chem: 546–551

  7. Narsaiah AV, Nagaiah K (2003) Synth Commun 21:3825

    Article  Google Scholar 

  8. Zhang XR, Chao W, Chuai YT, Ma Y, Hao R, Zou DC, Wei YG, Wang Y (2006) Org Lett 8:2563

    Article  CAS  Google Scholar 

  9. Radi M, Bernardo V, Bechi B, Castagnolo D, Pagano M, Botta M (2009) Tetrahedron Lett 47:6572

    Article  Google Scholar 

  10. Welton T (1999) Chem Rev 99:2071

    Article  CAS  Google Scholar 

  11. Parvulescu VI, Hardacre C (2007) Chem Rev 107:2615

    Article  CAS  Google Scholar 

  12. Wasserscheid P (2006) Nature 439:797

    Article  CAS  Google Scholar 

  13. Vieira RC, Falvey DE (2008) J Am Chem Soc 130:1552

    Article  CAS  Google Scholar 

  14. Saha D, Saha A, Ranu BC (2009) Green Chem 11:733

    Article  CAS  Google Scholar 

  15. Potdar MK, Mohile SS, Salunkhe MM (2001) Tetrahedron Lett 42:9285

    Article  CAS  Google Scholar 

  16. Khurana JM, Kumar S (2010) Monatsh Chem 141:561

    Article  CAS  Google Scholar 

  17. Li XZ, Lin Q, Ma L (2010) Ultrason Sonochem 5:752

    Article  Google Scholar 

  18. Akbari J, Heydari A, Kalhor HR, Kohan SA (2010) J Comb Chem 1:137

    Article  Google Scholar 

  19. Olivier JH, Camerel F, Selb J, Retailleau P, Ziessel R (2009) Chem Commun 9:1133

    Article  Google Scholar 

  20. Wang YY, Jiang D, Dai LY (2008) Catal Commun 9:2475

    Article  CAS  Google Scholar 

  21. Wang YY, Gong XX, Wang ZZ, Dai LY (2010) J Mol Catal A 322:7

    Article  CAS  Google Scholar 

  22. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven JrT, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P, Cross J B, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM W, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004

  23. Meng Z, D¨olle A, Caper WR (2002) J Mol Strut (Theo) 585: 119

    Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge Prof. Hua Liang Jiang at Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China for providing the Gaussian 03 program and helpful guidance. And we are thankful to the National Natural Science Foundation of China (No. 21003049, 21073064).

Author information

Authors and Affiliations

  1. College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan, 250014, People’s Republic of China

    Wei Li

  2. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, Shanghai, 200062, People’s Republic of China

    Yu Wang, Zhizhong Wang, Liyi Dai & Yuanyuan Wang

Authors
  1. Wei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhizhong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Liyi Dai
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuanyuan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yuanyuan Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, W., Wang, Y., Wang, Z. et al. Novel SO3H-Functionalized Ionic Liquids Based on Benzimidazolium Cation: Efficient and Recyclable Catalysts for One-Pot Synthesis of Biscoumarin Derivatives. Catal Lett 141, 1651–1658 (2011). https://doi.org/10.1007/s10562-011-0689-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-011-0689-9

Keywords

Search

Navigation