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A fast and green method for synthesis of tetrahydrobenzo[a]xanthene-11-ones using Ce(SO4)2·4H2O as a novel, reusable, heterogeneous catalyst

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Abstract

A fast, green, and efficient method for synthesis of tetrahydrobenzo[a]xanthene-11-ones by one-pot, three-component reaction of β-naphthol, aromatic aldehydes, and dimedone, using cerium(IV) sulfate tetrahydrate, Ce(SO4)2·4H2O, as an effective and novel inorganic solid acid catalyst under neat conditions is described. The catalyst is inexpensive and readily available and can be recovered conveniently and reused efficiently such that substantial catalytic activity still remains after the fifth run. Other advantages of this procedure are high yields, short reaction times, easy work-up, and absence of any volatile and hazardous organic solvents.

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References

  1. T. Hideu, JP 56005480. Chem. Abstr. 95, 80922b (1981)

    Google Scholar 

  2. C.G. Knight, T.J. Stephens, Biochem. 285, 683 (1989)

    Google Scholar 

  3. J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lakroix, Eur. J. Med. Chem. 13, 67 (1978)

    CAS  Google Scholar 

  4. G. Saint-Ruf, H.T. Hieu, J.P. Poupelin, Naturwissenschaften 62, 584 (1975)

    Article  CAS  Google Scholar 

  5. R.M. Ion, Prog. Catal. 2, 55 (1997)

    Google Scholar 

  6. R.M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, Acta. Biochim. Pol. 45, 833 (1998)

    CAS  Google Scholar 

  7. Y.M. Shchekotikhin, T.G. Nikolaeva, Chem. Heterocycl. Compd. 42, 28 (2006)

    Article  CAS  Google Scholar 

  8. S.A. Hilderbrand, R. Weissleder, Tetrahedron Lett. 48, 4383 (2007)

    Article  CAS  Google Scholar 

  9. G. Pohlers, J.C. Scaiano, Chem. Mater. 9, 3222 (1997)

    Article  CAS  Google Scholar 

  10. B. Lesch, S. Bräse, Angew. Chem. Int. Ed. 43, 115 (2004)

    Article  Google Scholar 

  11. Y.L. Shi, M. Shi, Synlett 2623 (2005)

  12. M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, Z. Asgari, A. Hasaninejad, C. R. Chim. 15, 719 (2012)

    Article  CAS  Google Scholar 

  13. M. Zakeri, M.M. Heravi, M. Saeedi, N. Karimi, H.A. Oskooie, N. Tavakoli-Hoseini, Chin. J. Chem. 29, 1441 (2011)

    Article  CAS  Google Scholar 

  14. D. Fang, J.M. Yang, Y.F. Cao, Res. Chem. Intermed. 39, 1745 (2013)

    Article  CAS  Google Scholar 

  15. N.V. Shitole, S.B. Sapkal, B.B. Shingate, M.S. Shingare, Bull. Korean Chem. Soc. 32, 35 (2011)

    Article  CAS  Google Scholar 

  16. L.P. Mo, H.L. Chen, J. Chin. Chem. Soc. 57, 157 (2010)

    Article  CAS  Google Scholar 

  17. Z.H. Zhang, P. Zhang, S.H. Yang, H.J. Wang, J. Deng, J. Chem. Sci. 122, 427 (2010)

    Article  CAS  Google Scholar 

  18. C.S. Sundar, K.U.M. Rao, N.B. Reddy, M.V.N. Reddy, S.S. Prasad, C.S. Reddy, Catal. Sci. Technol. 2, 1382 (2012)

    Google Scholar 

  19. S. Sudha, M.A. Pasha, Ultrason. Sonochem. 19, 994 (2012)

    Article  CAS  Google Scholar 

  20. Y.H. Liu, L. Li, J. Heterocycl. Chem. 49, 861 (2012)

    Article  CAS  Google Scholar 

  21. Z.H. Zhang, H.J. Wang, X.Q. Ren, Y.Y. Zhang, Monatsh. Chem. 140, 1481 (2009)

    Article  CAS  Google Scholar 

  22. V. Rama, K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 53, 1018 (2012)

    Article  CAS  Google Scholar 

  23. G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65, 7129 (2009)

    Article  CAS  Google Scholar 

  24. X.J. Sun, J.F. Zhou, P.S. Zhao, Synth. Commun. 42, 1542 (2012)

    Article  CAS  Google Scholar 

  25. H.J. Wang, X.Q. Ren, Y.Y. Zhang, Z.H. Zhang, J. Braz. Chem. Soc. 20, 1939 (2009)

    Article  CAS  Google Scholar 

  26. B. Maleki, M. Gholizadeh, Z. Sepehr, Bull. Korean Chem. Soc. 32, 1697 (2011)

    Article  CAS  Google Scholar 

  27. F. Nemati, M. Arghan, A. Amoozadeh, Synth. Commun. 42, 33 (2012)

    Article  CAS  Google Scholar 

  28. P.V. Shinde, A.H. Kategaonkar, B.B. Shingate, M.S. Shingare, Beilstein J. Org. Chem. 7, 53 (2011)

    Article  CAS  Google Scholar 

  29. J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 4777 (2009)

    Article  CAS  Google Scholar 

  30. J. Li, W. Tang, L. Lu, W. Su, Tetrahedron Lett. 49, 7117 (2008)

    Article  CAS  Google Scholar 

  31. M.M. Heravi, H. Alinejhad, K. Bakhtiari, H.A. Oskooie, Mol. Divers. 14, 621 (2010)

    Article  CAS  Google Scholar 

  32. B. Das, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, Synlett. 3107 (2007)

  33. T. Okuhara, Chem. Rev. 102, 3641 (2002)

    Article  CAS  Google Scholar 

  34. A. Davoodnia, M.M. Heravi, L. Rezaei-Daghigh, N. Tavakoli-Hoseini, Chin. J. Chem. 28, 429 (2010)

    Article  CAS  Google Scholar 

  35. E. Saburi, A. Davoodnia, N. Tavakoli-Hoseini, Synth. React. Inorg. Met. Org. Nano Met. Chem. 41, 1063 (2011)

    Article  CAS  Google Scholar 

  36. N.P. Selvam, P.T. Perumal, Tetrahedron Lett. 47, 7481 (2006)

    Article  CAS  Google Scholar 

  37. L. He, C.A. Horiuchi, Appl. Organometal. Chem. 13, 867 (1999)

    Article  CAS  Google Scholar 

  38. K. Itoh, S. Takahashi, T. Ueki, T. Sugiyama, T.T. Takahashi, C.A. Horiuchi, Tetrahedron Lett. 43, 7035 (2002)

    Article  CAS  Google Scholar 

  39. C.A. Horiuchi, T. Fukushima, N. Furuta, W. Chai, S. Ji, Y. Saito, C. Hashimoto, T.T. Takahashi, T. Sugiyama, A. Muto, Y. Sakata, S. Nozaki, J. Chem. Res. 270 (2003)

  40. A. Davoodnia, M. Bakavoli, N. Pooryaghoobi, M. Roshani, Heterocycl. Commun. 13, 323 (2007)

    Article  CAS  Google Scholar 

  41. A. Davoodnia, M. Roshani, E. Saleh-Nadim, M. Bakavoli, N. Tavakoli-Hoseini, Chin. Chem. Lett. 18, 1327 (2007)

    Article  CAS  Google Scholar 

  42. A. Davoodnia, M. Bakavoli, M. Bashash, M. Roshani, R. Zhiani, Turk. J. Chem. 31, 599 (2007)

    CAS  Google Scholar 

  43. A. Davoodnia, R. Zhiani, N. Tavakoli-Hoseini, Monatsh. Chem. 139, 1405 (2008)

    Article  CAS  Google Scholar 

  44. A. Davoodnia, M. Bakavoli, Sh Mohseni, N. Tavakoli-Hoseini, Monatsh. Chem. 139, 963 (2008)

    Article  CAS  Google Scholar 

  45. M. Roshani, A. Davoodnia, MSh Hedayat, M. Bakavoli, Phosphorus Sulfur Silicon 179, 1153 (2004)

    Article  CAS  Google Scholar 

  46. N. Seifi, M.H. Zahedi-Niaki, M. Reza Barzegari, A. Davoodnia, R. Zhiani, A.A. Kaju, J. Mol. Catal. A. Chem. 260, 77 (2006)

    Article  CAS  Google Scholar 

  47. N. Tavakoli-Hoseini, A. Davoodnia, Asian J. Chem. 22, 7197 (2010)

    CAS  Google Scholar 

  48. A. Davoodnia, Asian J. Chem. 22, 1595 (2010)

    CAS  Google Scholar 

  49. M.M. Heravi, M. Saeedi, N. Karimi, M. Zakeri, Y.S. Beheshtiha, A. Davoodnia, Synth. Commun. 40, 523 (2010)

    Article  CAS  Google Scholar 

  50. M. Zeinali-Dastmalbaf, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, A. Khojastehnezhad, H.A. Zamani, Bull. Korean Chem. Soc. 32, 656 (2011)

    Article  CAS  Google Scholar 

  51. A. Davoodnia, A. Tavakoli-Nishaburi, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 635 (2011)

    Article  CAS  Google Scholar 

  52. A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini, M. Zeinali-Dastmalbaf, Chin. J. Chem. 29, 297 (2011)

    Article  CAS  Google Scholar 

  53. A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)

    Article  CAS  Google Scholar 

  54. A. Davoodnia, A. Khojastehnezhad, M. Bakavoli, N. Tavakoli-Hoseini, Chin. J. Chem. 29, 978 (2011)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors express their gratitude to the Islamic Azad University, Mashhad Branch for its financial support.

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Correspondence to Abolghasem Davoodnia.

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Taghavi-Khorasani, F., Davoodnia, A. A fast and green method for synthesis of tetrahydrobenzo[a]xanthene-11-ones using Ce(SO4)2·4H2O as a novel, reusable, heterogeneous catalyst. Res Chem Intermed 41, 2415–2425 (2015). https://doi.org/10.1007/s11164-013-1356-0

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