Skip to main content
Log in

Chem-grafted Zn-SSA as an Efficient Heterogeneous Catalyst to Synthesize 2-Pyridinones

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn–SSA) was found to be a high efficient heterogeneous catalyst to solve this problem. Under Zn–SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.

Graphical Abstract

Improving chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn–SSA) was found to be efficient heterogeneous catalyst to solve this problem. Under Zn-SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.

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.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Stewart B, Wild CP (2014) World Cancer Report WHO

  2. Vousden KH, Lu X (2002) Nat Rev Cancer 2:594

    Article  CAS  Google Scholar 

  3. Tanaka K, Mimura M, Hojo D (2009) Tetrahedron 65:9008

    Article  CAS  Google Scholar 

  4. Sośnicki JG, Struk L, Idzik T, Maciejewska G (2014) Tetrahedron 70:8624

    Article  Google Scholar 

  5. Landais Y, Robert F, Godineau E, Huet L, Likhite N (2013) Tetrahedron 69:10073

    Article  CAS  Google Scholar 

  6. Núñez-Villanueva D, García-López MT, Martín-Martínez M, González-Muñiz R (2015) Org Biomol Chem 13:5195

    Article  Google Scholar 

  7. Gao ZH, Chen XY, Zhang HM, Ye S (2015) Chem Commun 51:12040

    Article  CAS  Google Scholar 

  8. Xie YY, Liu, Hu PP, Kong XL, Qiu DH, Xu JL, Hider RC, Zhou Tao (2013) Med Chem Res 22:2351

    Article  CAS  Google Scholar 

  9. Krauze A, Liepins E, Kalme Z, Pelcers J, Duburs G (1984) Khimiya Geterotsiklicheskikh Soedinenii 11:1504

    Google Scholar 

  10. Marugán MM, Martín N, Seoane C, Soto JL (1989) Liebigs Annalen der Chemie 2:145

    Article  Google Scholar 

  11. Pradhan K, Bhattacharyya P, Paul S, Das AR (2012) Tetrahedron Lett 53:5840

    Article  CAS  Google Scholar 

  12. Dehghan A, Singh S, Anary-Abbasinejad M, Hassanabadi A (2015) Res Chem Intermediat 41:1001

    Article  CAS  Google Scholar 

  13. Climent MJ, Corma A, Iborra S (2011) Chem Rev 111:1072

    Article  CAS  Google Scholar 

  14. Manna J, Roy B, Sharma P (2015) J Power Sources 275:727

    Article  CAS  Google Scholar 

  15. Mansoor SS, Aswin K, Logaiya K, Sudhan SPN (2014) J Taibah Univer Sci 8:265

    Article  Google Scholar 

  16. Debnath K, Pathak S, Pramanik A (2014) Tetrahedron Lett 55:1743

    Article  CAS  Google Scholar 

  17. Bakherad M, Keivanloo A, Siavashi M, Omidian M (2014) Chin Chem Lett 25:149

    Article  CAS  Google Scholar 

  18. Shaterian HR, Ghashang M, Feyzi M (2009) Appl Catal A-Gen 345:128

    Article  Google Scholar 

  19. Niknam K, Saberi D (2009) Appl Catal A-Gen 366:220

    Article  CAS  Google Scholar 

  20. Azizian J, Mohammadi AA, Karimi N, Mohammadizadeh MR, Karimi AR (2006) Catal Commun 7:752

    Article  CAS  Google Scholar 

  21. Mohammadpoor-Baltork I, Mirkhani V, Moghadam M, Tangestaninejad S, Zolfigol MA, Abdollahi-Alibeik M, Khosropour AR, Kargar H, Hojati SF (2008) Catal Commun 9:894

    Article  CAS  Google Scholar 

  22. Dabiri M, Salehi P, Baghbanzadeh M, Zolfigol MA, Agheb M, Heydari S (2008) Catal Commun 9:785

    Article  CAS  Google Scholar 

  23. Niknam K, Karami B, Zolfigol MA (2007) Catal Commun 8:1427

    Article  CAS  Google Scholar 

  24. Ghorbani-Choghamarani A, Zolfigol MA, Rastegar T (2009) Chin J Catal 30:273

    Article  CAS  Google Scholar 

  25. Habibi D, Zolfigol MA, Safaiee M, Shamsian A, Ghorbani-Choghamarani A (2009) Catal Commun 10:1257

    Article  CAS  Google Scholar 

  26. Tamaddon F, Kargar-Shooroki H, Jafari AA (2013) J Mol Catal A 368–369:66

    Article  Google Scholar 

  27. Reza Kiasat A, Davarpanah J J (2013) Mol. Catal. A-Chem 372: 46

  28. Zhang LJ, Yu JL, Wang WL, Li H, Xu DD, Bi YD, Liu FD (2014) Tetrahedron Lett 55:710

    Article  CAS  Google Scholar 

  29. Bhattacharyya P, Pradhan K, Paul S, Das AR (2012) Tetrahedron Lett 53:4687

    Article  CAS  Google Scholar 

  30. Li JR, Zhang LJ, Shi DX, Li Q, Wang D, Wang CX, Zhang Q, Zhang L, Fan YQ (2008) Synlett 2:233

    Article  Google Scholar 

  31. El Ashry ESH, El Kilany Y, Rashed N, Assafir H (1999) Adv Heterocyclic Chem 75:79

    Article  Google Scholar 

  32. Khazaei M, Anary-Abbasinejad M, Hassanabadi A, Sadeghi B (2012) E-J. Chem 9(2):615

    Article  CAS  Google Scholar 

  33. Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka CJ, Singh B Jr, Thielking WH, Williams GL, Lesher GY (1984) J Heterocyclic Chem 21:1849

    Article  CAS  Google Scholar 

  34. Seoane C, Soto JL, Zamorano P, Quinteiro M (1981) J Heterocyclic Chem 18:309

    Article  CAS  Google Scholar 

  35. Liu ZQ, Liu BK, Wu Q, Lin XF (2011) Tetrahedron 67:9736

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Tianjin Municipal Science and Technology Commission for its financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Li Jun Zhang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 339 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, L.J., Zhang, X., You, Z.S. et al. Chem-grafted Zn-SSA as an Efficient Heterogeneous Catalyst to Synthesize 2-Pyridinones. Catal Lett 146, 2081–2086 (2016). https://doi.org/10.1007/s10562-016-1806-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-016-1806-6

Keywords

Navigation