Skip to main content
SpringerLink
Log in

Silica-supported molybdic acid: preparation, characterization, and its catalytic application in synthesis of pyranocoumarins

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

Abstract

Silica-supported molybdic acid was employed as novel, recyclable, and safe catalyst in a one-pot three-component condensation of aldehydes, malononitrile, and 4-hydroxycoumarin to produce new and known pyrano[2,3-c]chromenes as potent biologically active compounds. This expedient new route has advantages, such as the use of a safe and reusable catalyst, simple operation, short reaction times, and good to excellent yields. The silica-supported molybdic acid as a novel solid acid was characterized by X-ray fluorescence, X-ray diffraction, and Fourier transform infrared spectroscopy.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Estevez V, Villacampa M, Menendez JC (2010) Chem Soc Rev 39:4402

    Article  CAS  Google Scholar 

  2. Gu Y (2012) Green Chem 14:2091

    Article  CAS  Google Scholar 

  3. Elinson MN, Ilovaisky AI, Merkulova VM, Belyakov PA, Chizhov AO (2010) Tetrahedron 66:4043

    Article  CAS  Google Scholar 

  4. Dekamin MG, Eslami M, Maleki A (2013) Tetrahedron 69:1074

    Article  CAS  Google Scholar 

  5. Mungra DC, Patel MP, Rajani DP, Patel RG (2011) Eur J Med Chem 46:4192

    Article  CAS  Google Scholar 

  6. Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517

    Article  CAS  Google Scholar 

  7. Cingolani GM, Gualtteri F, Pigin M (1961) J Med Chem 12:531

    Article  Google Scholar 

  8. Wu JYC, Fong WF, Zhang JX, Leung CH, Kwong HL, Yang MS, Li D, Cheung HY (2003) Eur J Pharmacol 473:9

    Article  CAS  Google Scholar 

  9. Perrella FW, Chen SF, Behrens DL, Kaltenbach RF, Seitz SP (1994) J Med Chem 37:2232

    Article  CAS  Google Scholar 

  10. Kashman Y, Gustafson KR, Fuller RW, Cardellina JH, McMahon JB, Currens MJ, Buckheit RW, Hughes SH, Gragg GM, Boyd MR (1992) J Med Chem 35:2735

    Article  CAS  Google Scholar 

  11. Andreani LL, Lapi E (1960) Chem Pharm Bull 99:583

    Google Scholar 

  12. Ellis GP (1977) The chemistry of heterocyclic compounds. Chromenes, chromanes and chromones. John Wiley, New York

    Google Scholar 

  13. Arnesto D, Horspool WM, Martin N, Ramos A, Seaone C (1989) J Org Chem 54:3069

    Article  Google Scholar 

  14. Khurana JM, Nand B, Saluja P (2010) Tetrahedron 66:5637

    Article  CAS  Google Scholar 

  15. Jin TS, Xiao JC, Wang SJ, Li TS (2004) Ultrason Sonochem 11:393

    CAS  Google Scholar 

  16. Jin TS, Zhang JS, Liu LB, Wang AQ, Li TS (2006) Synth Commun 36:2009

    Article  CAS  Google Scholar 

  17. Khurana JM, Kumar S (2009) Tetrahedron Lett 50:4125

    Article  CAS  Google Scholar 

  18. Da-Qing S, Jing W, Qi-Ya Z, Xiang-Shan W (2006) Chin J Org Chem 26:643

    Google Scholar 

  19. Al-Matar M, Khalil KD, Meier H, Kolshorn H, Elnagdi MH (2008) Arkivoc 16:288

    Google Scholar 

  20. Zhou Z, Yang F, Wu L, Zhang A (2012) Chem Soc Trans 1:57

    Article  CAS  Google Scholar 

  21. Naimi-jamal MR, Mashkouri S, Sharifi A (2010) Mol Divers 14:473

    Article  CAS  Google Scholar 

  22. Surpur MP, Kshirsagar S, Samant S (2008) Tetrahedron Lett 50:719

    Article  Google Scholar 

  23. Rad-Moghadam K, Yoseftabar-Miri L (2011) Tetrahedron 67:5693

    Article  CAS  Google Scholar 

  24. Peng Y, Song G (2007) Catal Commun 8:111

    Article  CAS  Google Scholar 

  25. Khurana MJ, Nand B, Saluja P (2010) Tetrahedron 66:5637

    Article  CAS  Google Scholar 

  26. Raghuvanshi DS, Singh KN (2010) Arkivoc 10:305

    Google Scholar 

  27. Dekamin MG, Varmira K, Farahmand M, Sagheb-Asl S, Karimi Z (2010) Catal Commun 12:226

    Article  CAS  Google Scholar 

  28. Cornelis A, Laszlo P (1985) Synthesis 10:909

    Article  Google Scholar 

  29. Karami B, Kiani M (2010) Catal Commun 14:62

    Article  Google Scholar 

  30. Karami B, Khodabakhshi S, Nikrooz N (2011) Polycycl Aromat Compd 31:97

    Article  CAS  Google Scholar 

  31. Montazerozohori M, Karami B (2006) Helv Chim Acta 89:2922

    Article  CAS  Google Scholar 

  32. Karade H, Sathe M, Kaushik MP (2007) Catal Commun 8:741

    Article  CAS  Google Scholar 

  33. Brezesinski T, Wang J, Tolbert SH, Dunn B (2010) Nat Mater 9:146

    Article  CAS  Google Scholar 

  34. Khodabakhshi S, Karami B, Baghernejad M (2014) Monatsh Chem 145:1839

    Article  CAS  Google Scholar 

  35. Kamaei V, Karami B, Khodabakhshi S (2014) Polycycl Aromat Compd 34:1

    Article  CAS  Google Scholar 

  36. Khodabakhshi S, Karami B, Eskandari K (2014) C R Chimie 17:35

    Article  CAS  Google Scholar 

  37. Karami B, Khodabakhshi S, Hashemi F (2013) Tetrahedron Lett 54:3583

    Article  CAS  Google Scholar 

  38. Karami B, Farahi M, Khodabakhshi S (2012) Helv Chim Acta 95:455

    Article  CAS  Google Scholar 

  39. Karami B, Eskandari K, Khodabakhshi S (2012) Arkivoc 9:76

    Google Scholar 

  40. Wang HJ, Lu J, Zhang ZH (2010) Monatsh Chem 141:1107

    Article  CAS  Google Scholar 

  41. Patra A, Mahapatra T (2012) J Indian Chem Soc 89:925

    CAS  Google Scholar 

  42. Khurana JM, Kumar S (2009) Tetrahedron Lett 50:4125

    Article  CAS  Google Scholar 

  43. Greenwood NA, Earnshaw N (1984) Chemistry of the elements. Pergamon, Oxford

    Google Scholar 

  44. Mehrabi H, Abusaidi H (2010) J Iran Chem Soc 78:890

    Article  Google Scholar 

  45. Abdolmohammadi S, Balalaie S (2007) Tetrahedron Lett 48:3299

    Article  CAS  Google Scholar 

  46. Xiang-Shan W, Zhao-Sen Z, Da-Qing S, Xian-Yong W, Zhi-Min Z (2005) Chin J Org Chem 25:1138

    Google Scholar 

Download references

Acknowledgments

We thank the Yasouj University for their support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Yasouj University, P. O. Box 353, Yasouj, 75918-74831, Iran

    Bahador Karami & Mahtab Kiani

Authors
  1. Bahador Karami
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mahtab Kiani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bahador Karami.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karami, B., Kiani, M. Silica-supported molybdic acid: preparation, characterization, and its catalytic application in synthesis of pyranocoumarins. Monatsh Chem 147, 1117–1124 (2016). https://doi.org/10.1007/s00706-015-1551-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1551-3

Keywords

Search

Navigation