Skip to main content
SpringerLink
Log in

Polyvinylsulfonic Acid: An Efficient, Water-Soluble and Reusable Brønsted Acid Catalyst for the Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones in Water and Ethanol

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A facile and environmentally benign protocol has been developed for the one-pot three-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones from the cyclocondensation reaction of aldehyde, ethyl acetoacetate (β-dicarbonyl compound) and urea or thiourea using polyvinylsulfonic acid as a reusable homogeneous Brønsted acid- and metal-free organocatalyst in water and ethanol. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple experimental and work-up procedure.

Graphical Abstract

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Kappe CO (1993) Tetrahedron 49:6937

    Article  CAS  Google Scholar 

  2. Folkers K, Johnson TB (1933) J Am Chem Soc 55:3784

    Article  CAS  Google Scholar 

  3. Kappe CO (1997) J Org Chem 62:7201

    Article  CAS  Google Scholar 

  4. Atwal KS, Moreland S (1991) Bioorg Med Chem Lett 1:291

    Article  CAS  Google Scholar 

  5. Groer GJ, Dzwonczyk S, Mcmullen DM, Normadinam CS, Sleph PG, Moreland SJ (1995) J Cardiovasc Pharmacol 26:289

    Article  Google Scholar 

  6. Kape CO (2000) Acc Chem Res 33:879

    Article  Google Scholar 

  7. Atwal KS, Rovnyak GC, Kimball SD, Floyd DM, Moreland S, Swanson BN, Gougoutas DZ, Schewartz J, Smillie KM, Malley MF (1990) J Med Chem 33:2629

    Article  CAS  Google Scholar 

  8. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A (1991) J Med Chem 34:806

    Article  CAS  Google Scholar 

  9. Klein E, DeBonis S, Thiede B, Skoufias DA, Kozielski F, Lebeau L (2007) Bioorg Med Chem 15:6474

    Article  CAS  Google Scholar 

  10. Biginelli P (1893) Gazz Chim Ital 23:360

    Google Scholar 

  11. Hu EH, Sidler DR, Dolling UH (1998) J Org Chem 63:3454

    Article  CAS  Google Scholar 

  12. Bose DS, Fatima L, Mereyala HB (2003) J Org Chem 68:587

    Article  CAS  Google Scholar 

  13. Ma Y, Qian C, Wang L, Yang M (2000) J Org Chem 65:3864

    Article  CAS  Google Scholar 

  14. Nandurkar NS, Bhanushali MJ, Bhor MD, Bhanage BM (2007) J Mol Catal A Chem 271:14

    Article  CAS  Google Scholar 

  15. Ramalinga K, Vijyalakshmi P, Kaimal TNB (2001) Synlett 863

  16. Paraska AS, Dewkar GK, Sudalai A (2003) Tetrahedron Lett 44:3305

    Article  Google Scholar 

  17. Lu J, Ma H (2000) Synlett 63

  18. Lu J, Bai Y (2002) Synthesis 466

  19. Bhosale RS, Bhosale SV, Bhosale SV, Wang T, Zubaidha PK (2004) Tetrahedron Lett 45:9111

    Article  CAS  Google Scholar 

  20. Liu C, Wang J, Li Y (2006) J Mol Catal A Chem 258:367

    Article  CAS  Google Scholar 

  21. Lu J, Bai Y, Wang Z, Yang B, Ma H (2000) Tetrahedron Lett 41:9075

    Article  CAS  Google Scholar 

  22. Reddy CV, Mahesh M, Raju PVK, Babu TR, Reddy VVN (2002) Tetrahedron Lett 43:2657

    Article  CAS  Google Scholar 

  23. Kumar KA, Kasthuraiah M, Reddy CS, Reddy CD (2001) Tetrahedron Lett 42:7873

    Article  Google Scholar 

  24. Yadav JS, Reddy BVS, Srinivas R, Venugopal C, Ramalingam T (2001) Synthesis 9:1341

    Article  Google Scholar 

  25. Salitha G, Reddy GSK, Reddy KB, Yadav JS (2003) Tetrahedron Lett 44:6497

    Article  Google Scholar 

  26. Zhang M, Li YQ (2006) Synth Commun 36:835

    Article  CAS  Google Scholar 

  27. Liu CJ, Wang JD (2009) Molecules 14:763

    Article  CAS  Google Scholar 

  28. Tu S, Fang F, Miao C, Jiang H, Feng Y, Shi D, Wang X (2003) Tetrahedron Lett 44:6153

    Article  CAS  Google Scholar 

  29. Jin T, Zhang S, Li T (2002) Synth Commun 32:1847

    Article  CAS  Google Scholar 

  30. Tu S, Fang F, Zhu S, Li T, Zhang X, Zhuang Q (2004) Synlett 537

  31. Takale S, Parab S, Phatangare K, Pisal R, Chaskar A (2011) Catal Sci Technol 1:1128

    Article  CAS  Google Scholar 

  32. Salehi P, Dabiri M, Zolfigol MA, Bodaghifard MA (2003) Tetrahedron Lett 44:2889

    Article  CAS  Google Scholar 

  33. Singh K, Arora D, Singh S (2006) Tetrahedron Lett 47:4205

    Article  CAS  Google Scholar 

  34. Rani RV, Srinias N, Kishan MR, Kulkarni SJ, Raghavan K (2003) Green Chem 3:305

    Article  Google Scholar 

  35. Jain SL, Joseph JK, Singhal S, Sain B (2007) J Mol Catal A Chem 268:134

    Article  CAS  Google Scholar 

  36. Bigi F, Carloni S, Frullanti B, Maggi R, Sartori G (1999) Tetrahedron Lett 40:3465

    Article  CAS  Google Scholar 

  37. Yadav JS, Reddy BVS, Sridhar P, Reddy JSS, Nagaiah K, Lingaiah N, Saiprasd PS (2004) Eur J Org Chem 552

  38. Reddy PN, Reddy YT, Reddy MN, Rajitha B, Crooks PA (2009) Synth Commun 39:1257

    Article  CAS  Google Scholar 

  39. Wang L, Cai C (2008) J Heterocycl Chem 45:1771

    Article  CAS  Google Scholar 

  40. Heravi MM, Bakhtiari L, Bamoharram FF (2006) Catal Commun 7:373

    Article  CAS  Google Scholar 

  41. Donadoni A, Massi A (2001) Tetrahedron Lett 42:7975

    Article  Google Scholar 

  42. Chandak HS, Lad NP, Upare PP (2009) Catal Lett 131:469

    Article  CAS  Google Scholar 

  43. Debache A, Amimour M, Belfaitah A, Rhouati S, Carboni B (2008) Tetrahedron Lett 49:6119

    Article  CAS  Google Scholar 

  44. Legeay JC, Eunde JJV, Bazureau JP (2005) Tetrahedron 61:12386

    Article  CAS  Google Scholar 

  45. Peng J, Deng Y (2001) Tetrahedron Lett 42:5917

    Article  CAS  Google Scholar 

  46. Polshettiwar V, Varma RS (2007) Tetrahedron Lett 48:7343

    Article  CAS  Google Scholar 

  47. Esenberg H, Mohan GR (1959) J Phys Chem 63:671

    Article  Google Scholar 

  48. Distler H (1965) Angew Chem Int Ed 4:300

    Article  Google Scholar 

  49. Okayasu T, Saito K, Nishide H, Hearn MTW (2009) Chem Commun 4708

  50. Mitsutani A (2002) Catal Today 73:57

    Article  CAS  Google Scholar 

  51. Hino M, Arata K (1985) Appl Catal 18:401

    Article  CAS  Google Scholar 

  52. Eliel EL, Fisk MT, Prosser T (1963) Org Synth 4:169

    Google Scholar 

  53. Kuma AK, Chottopadhyay TK (1987) Tetrahedron Lett 28:3713

    Article  Google Scholar 

  54. Koster R, Linden BV, Poels E, Blick A (2001) J Catal 204:333

    Article  CAS  Google Scholar 

  55. Rahmatpour A (2011) Monatsh Chem 142:1259

    Article  CAS  Google Scholar 

  56. Rahmatpour A (2011) React Funct Polym 71:80

    Article  CAS  Google Scholar 

  57. Rahmatpour A (2011) Heteroat Chem 22:51

    Article  CAS  Google Scholar 

  58. Rahmatpour A (2011) Heteroat Chem 22:85

    Article  CAS  Google Scholar 

  59. Rahmatpour A (2012) Monatsh Chem 143:491

    Article  CAS  Google Scholar 

  60. Breslow DS, Kutner A (1958) J Polym Sci 27:295

    Article  CAS  Google Scholar 

  61. Sakurada I, Sakaguchi Y, Ono T, Ueda T (1966) Die Makromol Chem 91:243

    Article  CAS  Google Scholar 

  62. Joseph JK, Jain SL, Sain B (2006) J Mol Catal A Chem 247:99

    Article  CAS  Google Scholar 

  63. Lin H, Zhao Q, Xu B, Wang X, Mole J (2007) J Mol Catal A Chem 268:221

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Polymer Science and Technology Division, Research Institute of Petroleum Industry (RIPI), 14665-1137, Tehran, Iran

    Ali Rahmatpour

Authors
  1. Ali Rahmatpour
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ali Rahmatpour.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rahmatpour, A. Polyvinylsulfonic Acid: An Efficient, Water-Soluble and Reusable Brønsted Acid Catalyst for the Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones in Water and Ethanol. Catal Lett 142, 1505–1511 (2012). https://doi.org/10.1007/s10562-012-0873-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-012-0873-6

Keywords

Search

Navigation