Skip to main content
Log in

A facile and efficient synthesis of tetrahydrobenzo[b]pyrans using lactose as a green catalyst

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Lactose has been used as a mild, efficient, green, and inexpensive catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives via a one-pot, three-component condensation between aryl aldehydes, malononitrile, and dimedone in H2O:EtOH at 60 °C. This method offers a considerable number of advantages including short reaction time, high to quantitative yields, low cost, easy accesses, and simple work-up.

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
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. G.P. Ellis, in The Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, ed. by A. Weissberger, E.C. Taylor (Wiley, New York, 1977), p. 11

    Chapter  Google Scholar 

  2. A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41 (2011)

    Article  CAS  Google Scholar 

  3. A. Shaabani, M. Mohammadpour Amini, S. Ghasemi, R. Ghadari, A.H. Rezayan, Y. Fazaeli, S. Feizi, Chem. Pharm. Bull. 58, 270 (2010)

    Article  CAS  Google Scholar 

  4. S. Banerjee, A. Horn, H. Khatri, G.A. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  5. S. Banerjee, G. Sereda, Tetrahedron Lett. 50, 6959 (2009)

    Article  CAS  Google Scholar 

  6. L. Alvey, S. Prado, V. Huteau, B. Saint-JonisMichel, S. Koch, S.M. Cole, F.T. Tillequin, Y.L. Janin, Bioorg. Med. Chem. 16, 8264 (2008)

    Article  CAS  Google Scholar 

  7. T. Symeonidis, M. Chamilos, D.J. Hadjipavlou-Litina, M. Kallitsakis, K.E. Litinas, Bioorg. Med. Lett. 19, 1139 (2009)

    Article  CAS  Google Scholar 

  8. T. Narender, S. Shweta Gupta, Bioorg. Med. Chem. Lett. 14, 3913 (2004)

    Article  CAS  Google Scholar 

  9. L. Lakshmi, K. Pandey, A. Kapil, N. Singh, M. Samant, A. Dube, Phytomedicine 14, 36 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. A.M. El-Agrody, M.H. El-Hakium, M.S. Abd El-Latif, A.H. Fekry, E.S.M. El-Sayed, K.A. El-Gareab, Acta Pharm. 50, 111 (2000)

    CAS  Google Scholar 

  12. C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J. Keana, Chem. Abstr. 134, 29313a (2001)

    Google Scholar 

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

    Article  Google Scholar 

  14. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  15. S.J. Tu, H. Jiang, Q.Y. Zhung, C.B. Miu, D.Q. Shi, X.S. Wang, Y. Gao, Chin. J. Org. Chem. 23, 488 (2003)

    CAS  Google Scholar 

  16. T.S. Jin, A.Q. Wang, F. Shi, L.S. Han, L.B. Liu, T.S. Li, ARKIVOC xiv, 78 (2006)

    Article  Google Scholar 

  17. S. Balalaie, M. Shiekh-Ahmadi, M. Barazjanian, Cat. Commun. 8, 1724 (2007)

    Article  CAS  Google Scholar 

  18. S. Abdolmohammadi, S. Balalaie, Tetrhedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  19. S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64, 9143 (2008)

    Article  CAS  Google Scholar 

  20. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

  21. R. Hekmatshor, S. Majedi, K. Bakhtiari, Cat. Commun. 9, 307 (2008)

    Article  Google Scholar 

  22. Y.M. Ren, C. Cai, Cat. Commun. 9, 1017 (2008)

    Article  Google Scholar 

  23. M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Cat. Commun. 10, 272 (2008)

    Article  CAS  Google Scholar 

  24. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  25. G. Shabitha, K. Harundhathi, K. Sudhakar, B.S. Sartry, J.S. Yadav, Synth. Commun. 39, 433 (2009)

    Article  Google Scholar 

  26. W.O. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40, 587 (2010)

    Article  CAS  Google Scholar 

  27. L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluor. Chem. 127, 97 (2006)

    Article  CAS  Google Scholar 

  28. M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth. Commun. 40, 1492 (2010)

    Article  CAS  Google Scholar 

  29. D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47, 63 (2010)

    CAS  Google Scholar 

  30. Y. Li, H. Chen, C. Shi, S. Ji, J. Comb. Chem. 12, 231 (2010)

    Article  CAS  Google Scholar 

  31. S.S. Katkar, M.K. Lande, B.R. Arbad, S.T. Gaikwad, Chin. J. Chem. 29, 199 (2011)

    Article  CAS  Google Scholar 

  32. J. Zheng, Y.Q. Li, Sch. Res. Libr. 3, 381 (2011)

    CAS  Google Scholar 

  33. P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S.H. Han, S.S. Kolekar, C. R. Chim. 14, 878 (2011)

    Article  CAS  Google Scholar 

  34. P.A. Grieco (ed.), Organic Synthesis in Water (Blackie Academic and Professional, London, 1998)

    Google Scholar 

  35. K. Ramesh, K. Karnakar, G. Satish, Y.V.D. Nageswar, Chin. Chem. Lett. 23, 1331 (2012)

    Article  CAS  Google Scholar 

  36. N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Mollashahi, Chin. J. Catal. (2014). doi:10.1016/S1872-2067(14)60003-6

    Google Scholar 

  37. M. Kangani, N. Hazeri, M. Maghsoodlou, S. Salahi, Res. Chem. Intermed. (2013). doi:10.107/s11164-013-1365-z

    Google Scholar 

  38. M.R. Mousavi, N. Hazeri, M.T. Maghsoodlou, S. Salahi, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 411 (2013)

    Article  CAS  Google Scholar 

  39. N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, M. Norouzi, M. Moin, S. Mohamadian-Souri, J. Chem. Res. 3, 550 (2013)

    Article  Google Scholar 

  40. T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S. Li, Synlett 5, 871 (2004)

    Article  Google Scholar 

  41. S. Gurumurthi, V. Sundari, R. Valliappan, Eur. J. Chem. 6, 466 (2009)

    Google Scholar 

  42. N.M.A. El -Rahaman, A.A. El-Kateb, M.F. Mady, Synth. Commun. 37, 3961 (2007)

    Article  Google Scholar 

Download references

Acknowledgments

We are thankful to the University of Sistan and Baluchestan Research Council for the partial support of this research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Malek Taher Maghsoodlou.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sadeh, F.N., Maghsoodlou, M.T., Hazeri, N. et al. A facile and efficient synthesis of tetrahydrobenzo[b]pyrans using lactose as a green catalyst. Res Chem Intermed 41, 5907–5914 (2015). https://doi.org/10.1007/s11164-014-1710-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1710-x

Keywords

Navigation