Skip to main content
SpringerLink
Log in

Bismuth triflate, Bi(OTf)3, as an efficient and reusable catalyst for synthesis of dihydropyrano[3,2-b]chromenediones

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Bi(OTf)3 was found to be an efficient, reusable and high yielding catalyst for the synthesis of dihydropyrano[3,2-b]chromenediones via the three-component reaction of aromatic aldehydes, kojic acid and 1,3-diones. The catalyst could be separated and recovered easily, and was reused for several runs without significant loss of its activity.

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
Scheme 3

Similar content being viewed by others

References

  1. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805–3809 (2009)

    Article  CAS  Google Scholar 

  2. A.M. Shestopalov, Y.M. Litvinov, L.A. Rodinovskaya, O.R. Malyshev, M.N. Semenova, V.V. Semenov, ACS Comb. Sci. 14, 484–490 (2012)

    Article  CAS  Google Scholar 

  3. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517–520 (1993)

    Article  CAS  Google Scholar 

  4. A.M. El-Nagger, A.M. Abdel-El-Salam, M.S.A. Latif, F.S.M. Ahmed, Pol. J. Chem. 55, 793–797 (1981)

    Google Scholar 

  5. S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724–1728 (2007)

    Article  CAS  Google Scholar 

  6. C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F. W. Keana, PCT Int Appl WO 0075123 (2000)

  7. L. Novotný, P. Rauko, M. Abdel-Hamid, A. Vachalkova, Neoplasma 46, 89–92 (1999)

    Google Scholar 

  8. Š. Baláž, M. Uher, J. Brtko, M. Veverka, J. Bransová, J. Dobias, M. Pódová, J. Buchvald, Folia Microbiol. 38, 387–391 (1993)

    Article  Google Scholar 

  9. M. Fickova, E. Pravdova, L. Rondhal, M. Uher, J. Brtko, J. Appl. Toxicol. 28, 554–559 (2008)

    Article  CAS  Google Scholar 

  10. H.S. Rho, S.M. Ahn, D.S. Yoo, M.K. Kim, D.H. Cho, J.Y. Cho, Bioorg. Med. Chem. Lett. 20, 6569–6571 (2010)

    Article  CAS  Google Scholar 

  11. B. Reddy, M.R. Reddy, G. Narasimhulu, J. Yadav, Tetrahedron Lett. 51, 5677–5679 (2010)

    Article  CAS  Google Scholar 

  12. C. Zhang, Y. Qu, J. Chem. 2013, 1–4 (2012)

    Google Scholar 

  13. W.L. Li, L.Q. Wu, F.L. Yan, J. Braz. Chem. Soc. 22, 2202–2205 (2011)

    Article  CAS  Google Scholar 

  14. L.F. Tietze, A. Modi, Med. Res. Rev. 20, 304–322 (2000)

    Article  CAS  Google Scholar 

  15. J.E. Biggs-Houck, A. Younai, J.T. Shaw, Curr. Opin. Chem. Biol. 14, 371–382 (2010)

    Article  CAS  Google Scholar 

  16. C. deGraaff, E. Ruijter, R.V.A. Orru, Chem. Soc. Rev. 41, 3969–4009 (2012)

    Article  CAS  Google Scholar 

  17. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083–3135 (2012)

    Article  Google Scholar 

  18. A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168–3210 (2000)

    Article  Google Scholar 

  19. N. Isambert, M.M.S. Duque, J.C. Plaquevent, Y. Génisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347–1357 (2011)

    Article  CAS  Google Scholar 

  20. J. Zhu, H. Bienaymé, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  21. N.M. Leonard, L.C. Wieland, R.S. Mohan, Tetrahedron 58, 8373–8397 (2002)

    Article  CAS  Google Scholar 

  22. P. Thirupathi, S.S. Kim, Tetrahedron 65, 5168–5173 (2009)

    Article  CAS  Google Scholar 

  23. S. Rivera, D. Bandyopadhyay, B.K. Banik, Tetrahedron Lett. 50, 5445–5448 (2009)

    Article  CAS  Google Scholar 

  24. S. Antoniotti, E. Duñach, C. R. Chim. 7, 679–688 (2004)

    Article  CAS  Google Scholar 

  25. I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, S. Baghersad, A. Mirjafari, C. R. Chim. 14, 944–952 (2011)

    Article  CAS  Google Scholar 

  26. Z. Wang, S. Fang, Eur. J. Org. Chem. 32, 5505–5508 (2009)

    Article  Google Scholar 

  27. H. Gaspard-Iloughmane, C. Le Roux, Eur. J. Org. Chem. 12, 2517–2532 (2004)

    Article  Google Scholar 

  28. E.D. Anderson, J.J. Ernat, M.P. Nguyen, A.C. Palma, R.S. Mohan, Tetrahedron Lett. 46, 7747–7750 (2005)

    Article  CAS  Google Scholar 

  29. F. Pin, S. Comesse, B. Garrigues, S. Marchalín, A. Daich, J. Org. Chem. 72, 1181–1191 (2007)

    Article  CAS  Google Scholar 

  30. P.W. Anzalone, A.R. Baru, E.M. Danielson, P.D. Hayes, M.P. Nguyen, A.F. Panico, R.C. Smith, R.S. Mohan, J. Org. Chem. 70, 2091–2096 (2005)

    Article  CAS  Google Scholar 

  31. T. Ollevier, V. Desyroy, B. Debailleul, S. Vaur, Eur. J. Org. Chem. 23, 4971–4973 (2005)

    Article  Google Scholar 

  32. I. Mohammadpoor-Baltork, A.R. Khosropour, S.F. Hojati, Synlett 18, 2747–2750 (2005)

    Article  Google Scholar 

  33. M. Rueping, B.J. Nachtsheim, W. Ieawsuwan, Adv. Synth. Catal. 348, 1033–1037 (2006)

    Article  CAS  Google Scholar 

  34. I. Mohammadpoor-Baltork, A.R. Khosropour, S.F. Hojati, Monat. Chem. 138, 663–667 (2007)

    Article  CAS  Google Scholar 

  35. T. Ollevier, Z. Li, Eur. J. Org. Chem. 34, 5665–5668 (2007)

    Article  Google Scholar 

  36. T. Ollevier, Z. Li, Adv. Synth. Catal. 351, 3251–3259 (2009)

    Article  CAS  Google Scholar 

  37. A.V. Narsaiah, B.V.S. Reddy, K. Premalatha, S.S. Reddy, J.S. Yadav, Catal. Lett. 131, 480–484 (2009)

    Article  Google Scholar 

  38. D.M. Podgorski, S.W. Krabbe, L.N. Le, P.R. Sierszulski, R.S. Mohan, Synthesis 16, 2771–2775 (2010)

    Google Scholar 

  39. S. Singh, A.D. Verma, R.D. Verma, Indian J. Chem. 22A, 814–818 (1983)

    CAS  Google Scholar 

  40. I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, K. Mohammadiannejad-Abbasabadi, H.R. Khavasi, Eur. J. Org. Chem. 7, 1357–1366 (2011)

    Article  Google Scholar 

  41. S. Anvar, I. Mohammadpoor-Baltork, S. Tangestaninejad, M. Moghadam, V. Mirkhani, A.R. Khosropour, R. Kia, RSC Adv. 2, 8713–8720 (2012)

    Article  CAS  Google Scholar 

  42. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal. 354, 3095–3104 (2012)

    Article  CAS  Google Scholar 

  43. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, New J. Chem. 37, 2037–2042 (2013)

    Article  CAS  Google Scholar 

  44. A. Landarani Isfahani, I. Mohammadpoor-Baltork, V. Mirkhani, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, R. Kia, Adv. Synth. Catal. 355, 957–972 (2013)

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Research Council of the University of Isfahan for financial support of this work.

Author information

Authors and Affiliations

  1. Catalysis Division, Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran

    Sara Pourshahrestani, Iraj Mohammadpoor-Baltork, Majid Moghadam, Shahram Tangestaninejad, Ahmad R. Khosropour & Valiollah Mirkhani

Authors
  1. Sara Pourshahrestani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Iraj Mohammadpoor-Baltork
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Majid Moghadam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shahram Tangestaninejad
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ahmad R. Khosropour
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Valiollah Mirkhani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Iraj Mohammadpoor-Baltork or Majid Moghadam.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pourshahrestani, S., Mohammadpoor-Baltork, I., Moghadam, M. et al. Bismuth triflate, Bi(OTf)3, as an efficient and reusable catalyst for synthesis of dihydropyrano[3,2-b]chromenediones. J IRAN CHEM SOC 12, 573–580 (2015). https://doi.org/10.1007/s13738-014-0514-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-014-0514-7

Keywords

Search

Navigation