Skip to main content
Log in

One-Pot Synthesis of 3,4-Dihydro-2(H)-Pyrimidinones Catalyzed by Reusable Acidic Choline-Based Ionic Liquids

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A series of choline-based ionic liquids (CIL) have been synthesized in this work. The results suggested that both the cations and the anions have significant influences on their properties such as thermostabilities, acidities and their performances for the synthesis of 3,4-dihydro-2(H)-pyrimidinones. The optimized catalytic system based on the CIL [DMEA][HSO4] for the Biginelli reactions benefits from the wide substrates tolerance, benign reaction conditions, easy work-up procedures, and the feasible reusability of the ionic liquid.

Graphical Abstract

The thermostabilities, acidities, and the catalytic activities for the Biginelli reactions are all follows the sequence of [DMEA][HSO4] > [Choline] [HSO4] > [DMEA][H2PO4] > [Choline] [H2PO4]

.

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004) J Am Chem Soc 126:9142

    Article  CAS  Google Scholar 

  2. Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC (2006) Angew Chem Int Ed 45:3904

    Article  CAS  Google Scholar 

  3. Nkuku CA, LeSuer RJ (2007) J Phys Chem B 111:13271

    Article  CAS  Google Scholar 

  4. Abbott AP, Bell TJ, Handa S, Stoddart B (2005) Green Chem 7:705

    Article  CAS  Google Scholar 

  5. Abbott AP, Nandhra S, Postlethwaite S, Smith EL, Ryder KS (2007) Phys Chem Chem Phys 9:3735

    Article  CAS  Google Scholar 

  6. Abbott AP, Frisch G, Hartley J, Ryder KS (2011) Green Chem 13:471

    Article  CAS  Google Scholar 

  7. Cooper ER, Andrews CD, Wheatley PS, Webb PB, Wormald P, Morris RE (2004) Nature 430:1012

    Article  CAS  Google Scholar 

  8. Parnham Emily R, Morris RE (2007) Acc Chem Res 40:1005

    Article  CAS  Google Scholar 

  9. Zhu AL, Liu RX, Li LJ, Li LY, Wang L, Wang JJ (2009) Catal Today 200:17–23

    Article  Google Scholar 

  10. Sunitha S, Kanjilal S, Reddy PS, Prasad RBN (2007) Tetrahedron Lett 48:6962

    Article  CAS  Google Scholar 

  11. Zhu AL, Li LJ, Wang JJ, Zhuo KL (2011) Green Chem 13:1244

    Article  CAS  Google Scholar 

  12. Kappe CO (1993) Tetrahedron 49:6931

    Article  Google Scholar 

  13. Sandhu S, Sandhu JS (2012) ARKIVOC 66

  14. Kim SS, Choi BS, Lee JH, Lee KK, Lee TH, Kim YH, Hyunik S (2009) Synlett 599

  15. Yamamoto K, Chen YG, Buono FG (2005) Org Lett 7:4673

    Article  CAS  Google Scholar 

  16. Chanetskyy B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884

    Article  Google Scholar 

  17. Panda SS, Khanna P, Khanna L (2012) Curr Org Chem 16:507

    Article  CAS  Google Scholar 

  18. Dewan M, Kumar A, Saxena A, De A, Mozumdar S (2012) PLoS ONE 7:e43978

    Article  Google Scholar 

  19. Ajbakhsh M, Mohajerani B, Heravi MM, Ahmadi AN (2005) J Mol Catal A 236:216

    Article  Google Scholar 

  20. Chen XH, Xu XY, Liu H, Cun LF, Gong LZ (2006) J Am Chem Soc 128:14802

    Article  CAS  Google Scholar 

  21. Kefayati H, Asghari F, Khanjanian R (2012) J Mol Liq 172:147

    Article  CAS  Google Scholar 

  22. Hajipour AR, Seddighi M (2012) Syn Commun 42:227

    Article  CAS  Google Scholar 

  23. Chen XF, Peng YQ (2008) Cat Lett 122:310

    Article  CAS  Google Scholar 

  24. Jain SL, Joseph JK, Sain B (2007) Cat Lett 115:52

    Article  CAS  Google Scholar 

  25. Gore S, Baskaran S, Koenig B (2011) Green Chem 13:1009

    Article  CAS  Google Scholar 

  26. Azizi N, Dezfuli S, Hahsemi MM (2012) Sci World J. doi:10.1100/2012/908702

    Google Scholar 

  27. Smith GP, Dworkin AS, Pagni RM, Zingg SP (1989) J Am Chem Soc 111:525

    Article  CAS  Google Scholar 

  28. King D, Mantz R, Osteryoung R (1996) J Am Chem Soc 118:11933

    Article  CAS  Google Scholar 

  29. Thomazeau C, OlivierBourbigou H, Magna L, Luts S, Gilbert B (2003) J Am Chem Soc 125:5264

    Article  CAS  Google Scholar 

  30. Seth D, Sarkar S, Sarkar N (2008) J Phys Chem B 112:2629

    Article  CAS  Google Scholar 

  31. Bahekar SS, Kotharkar SA, Shinde DB (2004) Mendeleev Commun 14:210

    Article  Google Scholar 

  32. Chavan SS, Sharama YO, Degani MS (2009) Green Chem Lett Rev 2:175

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by the National Natural Science Foundation of China (Grant 20903037, 21172058), and the Research Fund for the Doctoral Program of Higher Education of China (20094104120003).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jianji Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 11819 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhu, A., Li, Q., Li, L. et al. One-Pot Synthesis of 3,4-Dihydro-2(H)-Pyrimidinones Catalyzed by Reusable Acidic Choline-Based Ionic Liquids. Catal Lett 143, 463–468 (2013). https://doi.org/10.1007/s10562-013-0978-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-013-0978-6

Keywords

Navigation