Skip to main content
SpringerLink
Log in

Synthesis of dihydropyrano[2,3-c]pyrazoles using Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 as a new nano cooperative catalyst

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 was used as a nano cooperative catalyst for the synthesis of dihydropyrano[2,3-c]pyrazoles derivatives via a one-pot four component reaction of aldehyde, ethyl acetoacetate, malononitrile and hydrazine hydrate. The reactions were carried out at 70 °C under mild and heterogeneous conditions. The catalyst was easily synthesized by high energy ball milling and the effect of some parameters such as specific surface area, pore volume, particle size, pH and crystallinity degree of the catalyst was studied on the yield and reaction time. The used catalyst showed both Brønsted base and Lewis acid properties. The acidic sites were determined by FT-IR spectroscopy of pyridine adsorption technique at different temperature. Using a new cooperative catalyst and an environmentally benign procedure, good to high yield of the products and relatively short reaction time were the advantages of the present method.

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
Fig. 1
Fig. 2
Scheme 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Li M, Fang Z, Smith RL, Yang S (2016) Prog Energy Combust Sci 55:98–194

    Article  Google Scholar 

  2. Peters R (2015) Cooperative catalysis. Wiley, Weinheim

    Book  Google Scholar 

  3. Descamps M, Hornez JC, Leriche A (2009) J Eur Ceram Soc 29:369–375

    Article  CAS  Google Scholar 

  4. Mazaheri M, Haghighatzadeh M, Zahedi AM, Sadrnezhaad SK (2009) J Alloys Compd 471:180–184

    Article  CAS  Google Scholar 

  5. Arami H, Mohajerani M, Mazloumi M, Khalifehzadeh R, Lak A, Sadrnezhaad SK (2009) J Alloys Compd 469:391–394

    Article  CAS  Google Scholar 

  6. Wang J, Chao Y, Wan Q, Zhu Z, Yu H (2009) Acta Biomater 5:1798–1807

    Article  CAS  Google Scholar 

  7. Mostafa NY, Hassan HM, Mohamed FH (2009) J Alloys Compd 479:692–698

    Article  CAS  Google Scholar 

  8. Chen Y, Miao X (2004) Ceram Int 30:1961–1965

    Article  CAS  Google Scholar 

  9. Basar B, Tezcaner A, Keskin D, Evis Z (2010) Ceram Int 36:1633–1643

    Article  CAS  Google Scholar 

  10. Turkoza M, Atillab AO, Evisc Z (2013) Ceram Int 39:8925–8931

    Article  Google Scholar 

  11. Chen Y, Miao X (2005) Biomaterials 26:1205–1210

    Article  CAS  Google Scholar 

  12. Eslami H, Solati-Hashjin M, Tahriri M (2009) Mater Sci Eng C 29:1387–1398

    Article  CAS  Google Scholar 

  13. Fathi MH, Mohammadi Zahrani E (2009) J Cryst Growth 311:1392–1403

    Article  CAS  Google Scholar 

  14. Suchanek WL, Byrappa K, Shuk P, Riman RE, Janas VF, TenHuisen KS (2004) Biomaterials 25:4647–4657

    Article  CAS  Google Scholar 

  15. Mroz W, Bombalska A, Burdynska S, Jedynski M, Prokopiuk A, Budner B, Slosarczyk A, Zima A, Menaszek E, Scisłowska-Czarnecka A, Niedzielski K (2010) J Mol Struct 977:145–152

    Article  CAS  Google Scholar 

  16. Webster TJ, Ergun C, Doremus RH, Bizios R (2002) J Biomed Mater Res 59:312–317

    Article  CAS  Google Scholar 

  17. Sun ZP, Ercan B, Evis Z, Webster TJ (2010) J Biomed Mater Res 94A:806–815

    CAS  Google Scholar 

  18. Kheradmandfard M, Fathi MH (2010) J Alloys Compd 504:141–145

    Article  CAS  Google Scholar 

  19. Cai Y, Zhang S, Zeng X, Wang Y, Qian M, Weng W (2009) Thin Solid Films 517:5347–5351

    Article  CAS  Google Scholar 

  20. Portera AE, Patela N, Skepper JN, Best SM, Bonfield W (2003) Biomaterials 24:4609–4620

    Article  Google Scholar 

  21. Balamurugan A, Rebelo AHS, Lemos AF, Rocha JHG, Ventura JMG, Ferreira JMF (2008) Dent Mater 24:1374–1380

    Article  CAS  Google Scholar 

  22. Hijon N, Cabanas MV, Pena J, Vallet-Regi M (2006) Acta Biomater 2:567–574

    Article  Google Scholar 

  23. Aminian A, Solati-Hashjin M, Samadikuchaksaraei A, Bakhshi F, Gorjipour F, Farzadi A, Moztarzadeh F, Schmucker M (2011) Ceram Int 37:1219–1229

    Article  CAS  Google Scholar 

  24. Ahmadia T, Monshi A, Mortazavi V, Fathi MH, Sharifi S, HashemiBeni B, MoghareAbed A, Kheradmandfard M, Sharifnabi A (2014) Ceram Int 40:8341–8349

    Article  Google Scholar 

  25. Ragel CV, Vallet-Regí M, Rodríguez-Lorenzo LM (2002) Biomaterials 23:1865–1872

    Article  CAS  Google Scholar 

  26. Fathi MH, Zahrani EM (2008) Iran J Pharm Res 4:209–213

    Google Scholar 

  27. El-Tamany ES, El-Shahed FA, Mohamed BH (1999) J Serb Chem Soc 64:9–18

    CAS  Google Scholar 

  28. Ismail ZH, Aly GM, El-Degwi MS, Heiba HI, Ghorab MM (2003) Egypt J Biotechnol 13:73–82

    CAS  Google Scholar 

  29. Abdelrazak FM, Metz P, Kataeva O, Jager A, El-Mahrouky SF (2007) Arch Pharm Chem Life Sci 340:543–548

    Article  Google Scholar 

  30. Kuo SC, Huang LJ, Nakamura H (1984) J Med Chem 27:539–544

    Article  CAS  Google Scholar 

  31. Zaki MEA, Soliman HA, Hiekal OA, Rashad AEZ (2006) Naturoforsch C61:1–6

    Google Scholar 

  32. Wang JL, Liu D, Zheng ZJ, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z (2007) Proc Natl Acad Sci USA 97:7124–7129

    Article  Google Scholar 

  33. Foloppe N, Fisher LM, Howes R, Potter A, Robertos AGS, Surgenor AE (2006) Bioorg Med Chem 14:4792–4802

    Article  CAS  Google Scholar 

  34. Kashtoh H, Muhammad MT, Khan JJA, Rasheed S, Khan A, Perveen S, Javaid K, Wahab AT, Khan KM, Choudhary MI (2016) Bioorg Chem 65:61–72

    Article  CAS  Google Scholar 

  35. Litvinov YM, Shestopalov AA, Rodinovskaya LA, Shestopalov AM (2009) J Comb Chem 11:914–919

    Article  CAS  Google Scholar 

  36. Litvinov YM, Rodinovskaya LA, Shestopalov AM (2009) Russ Chem Bull Int Ed 58:2362–2368

    Article  CAS  Google Scholar 

  37. Vasuki G, Kumaravel K (2008) Tetrahedron Lett 49:5636–5638

    Article  CAS  Google Scholar 

  38. Mecadon H, Rohman MR, Kharbangar I, Laloo BM, Kharkongor I, Rajbangshi M, Myrboh B (2011) Tetrahedron Lett 52:3228–3231

    Article  CAS  Google Scholar 

  39. Siddekha A, Nizam A, Pasha MA (2011) Spectrochim Acta A 81:431–440

    Article  CAS  Google Scholar 

  40. Kanagaraj K, Pitchumani K (2010) Tetrahedron Lett 51:3312–3316

    Article  CAS  Google Scholar 

  41. Mecadon H, Rohman MR, Rajbangshi M, Myrboh B (2011) Tetrahedron Lett 52:2523–2525

    Article  CAS  Google Scholar 

  42. Kumar GS, Kurumurthy C, Veeraswamy B, Rao PS, Narsaiah B (2013) Organic Prep Proc Int 45:429–436

    Article  CAS  Google Scholar 

  43. Chavan HV, Babar SB, Hoval RU, Bandgar BP (2011) Bull Korean Chem Soc 32:3963–3966

    Article  CAS  Google Scholar 

  44. Bihani M, Bora PP, Bez G, Askari H (2013) Sustain Chem Eng 1:440–447

    Article  CAS  Google Scholar 

  45. Khurana JM, Chaudhary A (2012) Green Chem Lett Rev 5:633–638

    Article  CAS  Google Scholar 

  46. Ebrahimi J, Mohanndi A, Pakjoo V, Bahramzadeh E, Habibi A (2012) J Chem Sci 124:1013–1017

    Article  CAS  Google Scholar 

  47. Khazdooz L, Zarei A (2016) Iran J Catal 6:69–74

    Google Scholar 

  48. Guo RY, An ZM, Mo LP, Yang ST, Liu HX, Wang SX, Zhang ZH (2013) Tetrahedron 69:9931–9938

    Article  CAS  Google Scholar 

  49. Tamaddon F, Alizadeh M (2014) Tetrahedron Lett 55:3588–3591

    Article  CAS  Google Scholar 

  50. Maleki B, Nasiri N, Tayebee R, Khojastehnezhad A, Akhlaghi HA (2016) RSC Adv 6:79128–79134

    Article  CAS  Google Scholar 

  51. Bora PP, Bihani M, Bez G (2013) J Mol Catal B 92:24–33

    Article  CAS  Google Scholar 

  52. Tyagi B, Chudasama CD, Jasra RV (2006) Appl Clay Sci 31:16–28

    Article  CAS  Google Scholar 

  53. Ho TL (1977) Hard and soft acid and bases principle in organic chemistry. Academic Press, New York

    Google Scholar 

  54. Carey FA, Sundberg RJ (1990) Advanced organic chemistry, part B: reactions and synthesis, 3rd edn. Plenum Press, New York and London

    Book  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the funding support received for this project from the Islamic Azad University, Khorasgan and fasa Branches.

Author information

Authors and Affiliations

  1. Department of Science, Khorasgan (Isfahan) Branch, Islamic Azad University, Isfahan, 81595-158, Iran

    Leila Khazdooz

  2. Department of Science, Fasa Branch, Islamic Azad University, PO Box No. 364, Fasa, Fars, 7461713591, Iran

    Amin Zarei

  3. Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 311-86145, Iran

    Tahmineh Ahmadi, Hamidreza Aghaei, Nasrin Nazempour & Laleh Golestanifar

  4. Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, PO Box No. 517, Najafabad, Isfahan, 8514143131, Iran

    Nafisehsadat Sheikhan

Authors
  1. Leila Khazdooz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amin Zarei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tahmineh Ahmadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hamidreza Aghaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Nasrin Nazempour
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Laleh Golestanifar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Nafisehsadat Sheikhan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Leila Khazdooz.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1991 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khazdooz, L., Zarei, A., Ahmadi, T. et al. Synthesis of dihydropyrano[2,3-c]pyrazoles using Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 as a new nano cooperative catalyst. Reac Kinet Mech Cat 122, 229–245 (2017). https://doi.org/10.1007/s11144-017-1217-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-017-1217-8

Keywords

Search

Navigation