Skip to main content
Log in

Green and recyclable sulfonated graphene and graphene oxide nanosheet catalysts for the syntheses of 3,4-dihydropyrimidinones

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

Abstract

Sulfated graphene and graphene oxide were used successfully as the heterogeneous catalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones (-thiones) through the reaction between ethyl acetoacetate, an aldehyde, and an urea or thiourea, at room temperature in the environmentally friendly solvent. The catalysts could be separated from the reaction mixture and reused at least five times without any considerable loss of the activity. Sulfonated graphene proved to be a more efficient catalyst compared with graphene oxide.

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.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Biginelli P (1891) Ber Deutsch Chem Ges 24:1317

    Article  Google Scholar 

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

    Google Scholar 

  3. Biginelli P (1891) Ber Deutsch Chem Ges 24:2962

    Article  Google Scholar 

  4. Biginelli P (1893) Ber Deutsch Chem Ges 26:447

    Article  Google Scholar 

  5. Ashok M, Holla BS, Kumari NS (2007) Eur J Med Chem 42:380

    Article  CAS  Google Scholar 

  6. Hurst EW, Hull R (1961) J Med Pharm Chem 3:215

    Article  CAS  Google Scholar 

  7. Bahekar SS, Shinde DB (2004) Bioorg Med Chem Lett 14:1733

    Article  CAS  Google Scholar 

  8. Blacquiere JM, Sicora O, Vogels CM, Cuperlovic-Culf M, Decken A, Ouellette RJ, Westcott SA (2005) Can J Chem 83:2052

    Article  CAS  Google Scholar 

  9. Kato T, Chiba T, Abe Y (1984) 5-Carbamoyl-6-methyl-4-substituted-1,2,3,4-tetrahydro-2-thioxopyrimidines. Jpn Pat. 59190974, Oct 29, 1984; (1985) Chem Abstr 102:132067

  10. Fewell SW, Smith CM, Lyon MA, Dumitrescu TP, Wipf P, Day BW, Brodsky JL (2004) J Biol Chem 279:51131

    Article  CAS  Google Scholar 

  11. Rodina A, Vilenchik M, Moulick K, Aguirre J, Kim J, Chiang A, Litz J, Clement CC, Kang Y, She Y, Wu N, Felts S, Wipf P, Massague J, Jiang X, Brodsky JL, Krystal GW, Chiosis G (2007) Nat Chem Biol 3:498

    Article  CAS  Google Scholar 

  12. Evans CG, Wisen S, Gestwicki JE (2006) J Biol Chem 281:33182

    Article  CAS  Google Scholar 

  13. Wisen S, Androsavich J, Evans CG, Chang L, Gestwicki JE (2008) Bioorg Med Chem Lett 18:60

    Article  CAS  Google Scholar 

  14. Magerramov AM, Kurbanova MM, Abdinbekova RT, Rzaeva IA, Farzaliev VM, Allakhverdiev MA (2006) Russ J Appl Chem 79:787

    Article  CAS  Google Scholar 

  15. Kappe CO (2000) Eur J Med Chem 35:1043

    Article  CAS  Google Scholar 

  16. Grover GJ, Dzwonczyk S, McMullen DM, Normadinam CS, Sleph PG, Moreland S (1995) J Cardiovasc Pharmacol 26:289

    Article  CAS  Google Scholar 

  17. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC (1991) J Med Chem 34:806

    Article  CAS  Google Scholar 

  18. Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O’Reilly BC, Schwartz J, Malley MF (1992) J Med Chem 35:3254

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  20. Atwal KS, Rovnyak GC, Schwatz J, Moreland S, Hedberg A, Gougoutas JZ, Malley MF, Floyd DF (1990) J Med Chem 33:1510

    Article  CAS  Google Scholar 

  21. Baldwin JJ, Pitzenberger SM, McClure DE (1987) Substituted pyrimidinecarboxylates useful as calcium channel blockers. US Pat. 4675321, Jun 23, 1987; (1987) Chem Abstr 107:242619

  22. Ertan M, Balkan A, Saraç S, Uma S, Renaud JF, Rollad Y (1991) Arch Pharm 324:135

    Article  CAS  Google Scholar 

  23. Kastron VV, Vitolin RO, Khanina EL, Dubur GY, Kimenis AA, Kondratenko NV, Popov VI, Yagupolsky LM, Kolomeitsev AA (1988) Preparation of 2-oxo-4-(2′-difluoromethylthiophenyl)-5-methoxycarbonyl-6-methyl-1,2,3,4-tetrahydropyrimidine having coronary-dilating activity. US Pat. 4738965, Apr 19, 1988; (1989) Chem Abstr 110:18547

  24. Rovnyak GC, Kimball SD, Beyer B, Cucinotta G, DiMarco JD, Gougoutas J, Hedberg A, Malley M, McCarthy JP, Zhang R, Moreland S (1995) J Med Chem 38:119

    Article  CAS  Google Scholar 

  25. Sujatha K, Shanmugam P, Perumal PT, Muralidharan D, Rajendran M (2006) Bioorg Med Chem Lett 16:4893

    Article  CAS  Google Scholar 

  26. Yarim M, Sarac S, Kilic FS, Erol K (2003) Farmaco 58:17

    Article  CAS  Google Scholar 

  27. Saraç S, Ciftçi M, Zorkun IS, Tunç O, Erol K (2007) Arzneim-Forsch/Drug Res 57:137

    Google Scholar 

  28. Kolosov MA, Orlov VD, Beloborodov DA, Dotsenko VV (2009) Mol Divers 13:5

    Article  CAS  Google Scholar 

  29. Zhang Y-Q, Wang C, Li G-S, Li J-C, Liu H-M, Wu Q-H (2005) Chin J Org Chem 25:1265

    CAS  Google Scholar 

  30. Moghaddas M, Davoodnia A, Heravi MM, Tavakoli-Hoseini N (2012) Chin J Chem 33:706

    CAS  Google Scholar 

  31. Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V, Ezhilarasi MR (2008) Lett Org Chem 5:142

    Article  CAS  Google Scholar 

  32. Martínez S, Meseguer M, Casas L, Rodríguez E, Molins E, Moreno-Manas M, Roig A, Sabastián RM, Vallribera A (2003) Tetrahedron 59:1553

    Article  Google Scholar 

  33. Sabitha G, Reddy KB, Yadav JS, Shailaja D, Sivudu KS (2005) Tetrahedron Lett 46:8221

    Article  CAS  Google Scholar 

  34. Novoselov KS, Geim AK, Morozov S, Jiang D, Zhang Y, Dubonos S, Grigorieva I, Firsov A (2004) Science 306:666

    Article  CAS  Google Scholar 

  35. Schedin F, Geim A, Morozov S, Hill E, Blake P, Katsnelson M, Novoselov K (2007) Nature Mater 6:652

    Article  CAS  Google Scholar 

  36. Novoselov K, Jiang SZ, Zhang Y, Morozov S, Stormer H, Zeitler U, Maan J, Boebinger G, Kim P, Geim A (2007) Science 315:1379

    Article  CAS  Google Scholar 

  37. Wu J, Pisula W, Müllen K (2007) Chem Rev 107:718

    Article  CAS  Google Scholar 

  38. Liu F, Sun J, Zhu L, Meng X, Qi C, Xiao F-S (2012) J Mater Chem 22:5495

    Article  CAS  Google Scholar 

  39. Huang L, Wu B, Yu G, Liu Y (2011) J Mater Chem 21:919

    Article  CAS  Google Scholar 

  40. Feng D, Gu ZY, Li JR, Jiang HL, Wei ZH, Zhou C (2012) Angew Chem Int Ed 124:10453

    Article  Google Scholar 

  41. Hosseinzadeh-Khanmiri R, Moghimi A, Shaabani A, Valizadeh H, Seik WN (2014) Mol Divers 18:769

    Article  Google Scholar 

  42. Moghimi A, Hosseinzadeh-Khanmiri R, Omrani I, Shaabani A (2013) Tetrahedron Lett 54:3956

    Article  CAS  Google Scholar 

  43. Moghimi A, Hosseinzadeh-Khanmiri R, Shaabani A, Hamadani H (2013) J Iran Chem Soc 10:929

    Article  CAS  Google Scholar 

  44. Hassanpour A, Abolhasani J, Hosseinzadeh-Khanmiri R (2014) J Korean Chem Soc 58:5

    Article  Google Scholar 

  45. Xu Z, Dietrich J, Shaw AY, Hulme C (2010) Tetrahedron Lett 51:4566

    Article  CAS  Google Scholar 

  46. Zhang Y-M, Fan X, Yang S-M, Scannevin RH, Burke SL, Rhodes KJ, Jackson PF (2008) Bioorg Med Chem Lett 18:405

    Article  CAS  Google Scholar 

  47. Long D, Li W, Ling L, Miyawaki J, Mochida I, Yoon S-H (2010) Langmuir 26:16096

    Article  CAS  Google Scholar 

  48. Si Y, Samulski ET (2008) Nano Lett 8:1679

    Article  CAS  Google Scholar 

  49. Hummers WS, Offeman RE (1958) J Am Chem Soc 80:1339

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank, Marand Branch, Islamic Azad University, Marand, Iran for the financial support of this research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Akbar Hassanpour.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2184 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vessally, E., Hassanpour, A., Hosseinzadeh-Khanmiri, R. et al. Green and recyclable sulfonated graphene and graphene oxide nanosheet catalysts for the syntheses of 3,4-dihydropyrimidinones. Monatsh Chem 148, 321–326 (2017). https://doi.org/10.1007/s00706-016-1762-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1762-2

Keywords

Navigation