Catalysis Letters

, Volume 143, Issue 5, pp 463–468 | Cite as

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

  • Anlian Zhu
  • Qianqian Li
  • Lingjun Li
  • Jianji Wang


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]


Choline-based ionic liquids Thermostabilities Acidities Biginelli reactions 3,4-Dihydro-2(H)-pyrimidinones 



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).

Supplementary material

10562_2013_978_MOESM1_ESM.doc (11.5 mb)
Supplementary material 1 (DOC 11819 kb)


  1. 1.
    Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004) J Am Chem Soc 126:9142CrossRefGoogle Scholar
  2. 2.
    Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC (2006) Angew Chem Int Ed 45:3904CrossRefGoogle Scholar
  3. 3.
    Nkuku CA, LeSuer RJ (2007) J Phys Chem B 111:13271CrossRefGoogle Scholar
  4. 4.
    Abbott AP, Bell TJ, Handa S, Stoddart B (2005) Green Chem 7:705CrossRefGoogle Scholar
  5. 5.
    Abbott AP, Nandhra S, Postlethwaite S, Smith EL, Ryder KS (2007) Phys Chem Chem Phys 9:3735CrossRefGoogle Scholar
  6. 6.
    Abbott AP, Frisch G, Hartley J, Ryder KS (2011) Green Chem 13:471CrossRefGoogle Scholar
  7. 7.
    Cooper ER, Andrews CD, Wheatley PS, Webb PB, Wormald P, Morris RE (2004) Nature 430:1012CrossRefGoogle Scholar
  8. 8.
    Parnham Emily R, Morris RE (2007) Acc Chem Res 40:1005CrossRefGoogle Scholar
  9. 9.
    Zhu AL, Liu RX, Li LJ, Li LY, Wang L, Wang JJ (2009) Catal Today 200:17–23CrossRefGoogle Scholar
  10. 10.
    Sunitha S, Kanjilal S, Reddy PS, Prasad RBN (2007) Tetrahedron Lett 48:6962CrossRefGoogle Scholar
  11. 11.
    Zhu AL, Li LJ, Wang JJ, Zhuo KL (2011) Green Chem 13:1244CrossRefGoogle Scholar
  12. 12.
    Kappe CO (1993) Tetrahedron 49:6931CrossRefGoogle Scholar
  13. 13.
    Sandhu S, Sandhu JS (2012) ARKIVOC 66Google Scholar
  14. 14.
    Kim SS, Choi BS, Lee JH, Lee KK, Lee TH, Kim YH, Hyunik S (2009) Synlett 599Google Scholar
  15. 15.
    Yamamoto K, Chen YG, Buono FG (2005) Org Lett 7:4673CrossRefGoogle Scholar
  16. 16.
    Chanetskyy B, Dallinger D, Kappe CO (2004) J Comb Chem 6:884CrossRefGoogle Scholar
  17. 17.
    Panda SS, Khanna P, Khanna L (2012) Curr Org Chem 16:507CrossRefGoogle Scholar
  18. 18.
    Dewan M, Kumar A, Saxena A, De A, Mozumdar S (2012) PLoS ONE 7:e43978CrossRefGoogle Scholar
  19. 19.
    Ajbakhsh M, Mohajerani B, Heravi MM, Ahmadi AN (2005) J Mol Catal A 236:216CrossRefGoogle Scholar
  20. 20.
    Chen XH, Xu XY, Liu H, Cun LF, Gong LZ (2006) J Am Chem Soc 128:14802CrossRefGoogle Scholar
  21. 21.
    Kefayati H, Asghari F, Khanjanian R (2012) J Mol Liq 172:147CrossRefGoogle Scholar
  22. 22.
    Hajipour AR, Seddighi M (2012) Syn Commun 42:227CrossRefGoogle Scholar
  23. 23.
    Chen XF, Peng YQ (2008) Cat Lett 122:310CrossRefGoogle Scholar
  24. 24.
    Jain SL, Joseph JK, Sain B (2007) Cat Lett 115:52CrossRefGoogle Scholar
  25. 25.
    Gore S, Baskaran S, Koenig B (2011) Green Chem 13:1009CrossRefGoogle Scholar
  26. 26.
    Azizi N, Dezfuli S, Hahsemi MM (2012) Sci World J. doi: 10.1100/2012/908702 Google Scholar
  27. 27.
    Smith GP, Dworkin AS, Pagni RM, Zingg SP (1989) J Am Chem Soc 111:525CrossRefGoogle Scholar
  28. 28.
    King D, Mantz R, Osteryoung R (1996) J Am Chem Soc 118:11933CrossRefGoogle Scholar
  29. 29.
    Thomazeau C, OlivierBourbigou H, Magna L, Luts S, Gilbert B (2003) J Am Chem Soc 125:5264CrossRefGoogle Scholar
  30. 30.
    Seth D, Sarkar S, Sarkar N (2008) J Phys Chem B 112:2629CrossRefGoogle Scholar
  31. 31.
    Bahekar SS, Kotharkar SA, Shinde DB (2004) Mendeleev Commun 14:210CrossRefGoogle Scholar
  32. 32.
    Chavan SS, Sharama YO, Degani MS (2009) Green Chem Lett Rev 2:175CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Anlian Zhu
    • 1
  • Qianqian Li
    • 1
  • Lingjun Li
    • 1
  • Jianji Wang
    • 1
  1. 1.School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal UniversityXinxiangPeople’s Republic of China

Personalised recommendations