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Nano Sulfated Titania as a Heterogeneous Solid Acid Catalyst for the Synthesis of Pyrroles by Clauson–Kaas Condensation under Solvent-free Conditions

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Chemistry of Heterocyclic Compounds Aims and scope

A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-dimethoxytetrahydrofuran with amines and diamines in the presence of nano sulfated titania under solvent-free conditions is presented. This new protocol features simple operation, easy availability, stability, and eco-friendliness of catalyst, as well as high to excellent yields of products. In addition, we report for the first time an alternative method for the synthesis of pyrroles from aromatic amines containing the β-lactam fragment using nano sulfated titania as catalyst.

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References

  1. D. L. Boger, C. W. Boyce, M. A. Labroli, C. A. Sehon, and Q. Jin, J. Am. Chem. Soc., 121, 54 (1999).

    Article  CAS  Google Scholar 

  2. J. T. Gupton, Top. Heterocycl. Chem., 2, 53 (2006).

    CAS  Google Scholar 

  3. H. Fan, J. Peng, M. T. Hamann, and J. F. Hu, Chem. Rev., 108, 264 (2008).

    Article  CAS  Google Scholar 

  4. F. Aydogan, M. Basarir, C. Yolacan, and A. S. Demir, Tetrahedron, 63, 9746 (2007).

    Article  CAS  Google Scholar 

  5. R. Paolesse, S. Nardis, F. Sagone, and R. G. Khoury, J. Org. Chem., 66, 550 (2001).

    Article  CAS  Google Scholar 

  6. R. K. Dieter and H. Yu, Org. Lett., 2, 2283 (2000).

    Article  CAS  Google Scholar 

  7. M. Yamagishi, K. Nishigai, T. Hata, and H. Urabe, Org. Lett., 13, 4873 (2011).

    Article  CAS  Google Scholar 

  8. Furstner, H. Weintritt, and A. Hupperts, J. Org. Chem., 60, 6637 (1995).

    Article  Google Scholar 

  9. Freifeld, H. Shojaei, and P. Langer, J. Org. Chem., 71, 4965 (2006).

    Google Scholar 

  10. Eftekhari-Sis, M. Zirak, and A. Akbari, Chem. Rev., 113, 2958 (2013).

  11. E. Ghabraie, S. Balalaie, M. Bararjanian, H. R. Bijanzadeh, and F. Rominger, Tetrahedron, 67, 5415 (2011).

    Article  CAS  Google Scholar 

  12. V. Estévez, M. Villacampa, and J. C. Menéndez, Chem. Soc. Rev., 39, 4402 (2010).

    Article  Google Scholar 

  13. A. Jafari, H. Mahmoudi, and B. F. Mirjalili, J. Iran. Chem. Soc., 8, 851 (2011).

    Article  CAS  Google Scholar 

  14. P. Mundy, M. G. Ellerd, and F. G. Favaloro, Jr., Name Reactions and Reagents in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. (2005), p. 476.

  15. T. Maehara, R. Kanno, S. Yokoshima, and T. Fukuyama, Org. Lett., 14, 1946 (2012).

    Article  CAS  Google Scholar 

  16. G. Dou, C. Shi, and D. Shi, J. Comb. Chem., 10, 810 (2008).

    Article  CAS  Google Scholar 

  17. H. Veisi and S. Hemmati, J. Chin. Chem. Soc., 56, 240 (2009).

    CAS  Google Scholar 

  18. S. Handy and K. Lavender, Tetrahedron Lett., 54, 4377 (2013).

    Article  CAS  Google Scholar 

  19. L. Gao, L. Bing, Z. Zhang, H. Kecheng, H. Xiaoyun, and K. Deng, J. Organomet. Chem., 735, 26 (2013).

    Article  CAS  Google Scholar 

  20. B. S. Gourlay, P. P. Molesworth, J. H. Ryan, and J. A. Smith, Tetrahedron Lett., 47, 799 (2006).

    Article  CAS  Google Scholar 

  21. C. Miles, S. M. Mays, B. K. Southerland, T. J. Auvil, and D. M. Ketcha, ARKIVOC, xiv, 181 (2009).

  22. R. Bharadwaj and K. A. Scheidt, Org. Lett., 6, 2465 (2004).

    Article  CAS  Google Scholar 

  23. C. Silveira, M. P. Fortes, and S. R. Mendes, Curr. Org. Chem., 16, 1540 (2012).

    Article  CAS  Google Scholar 

  24. F. Aydogan and C. Yolacan, J. Chem. (2013). http://dx.doi.org/10.1155/2013/976724.

  25. M. Abid, L. Teixeira, and B. Török, Tetrahedron Lett., 48, 4047 (2007).

    Article  CAS  Google Scholar 

  26. M. Abid, S. M. Landge, and B. Török, Org. Prep. Proced. Int., 38, 495 (2006).

    Article  CAS  Google Scholar 

  27. C. Rochais, V. Lisowski, P. Dallemagne, and S. Rault, Tetrahedron Lett., 45, 6353 (2004).

    Article  CAS  Google Scholar 

  28. N. Azizi, A. Khajeh-Amiri, H. Ghafuri, M. Bolourtchian, and M. R. Saidi, Synlett, 2245 (2009).

    Google Scholar 

  29. S. Rivera, D. Bandyopadhyay, and B. K. Banik, Tetrahedron Lett., 50, 5445 (2009).

    Article  CAS  Google Scholar 

  30. X. Zhang and J. Shi, Tetrahedron, 67, 898 (2011).

    Article  CAS  Google Scholar 

  31. Aghapoor, L. Ebadi-Nia, F. Mohsenzadeh, M. M. Morad, Y. Balavar, and H. R. Darabi, J. Organomet. Chem., 708, 25 (2012).

    Article  Google Scholar 

  32. H. Veisi, Tetrahedron Lett., 51, 2109 (2010).

    Article  CAS  Google Scholar 

  33. J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, and W. Su, Tetrahedron Lett., 47, 5383 (2006).

    Article  CAS  Google Scholar 

  34. D. Bandyopadhyay, S. Mukherjee, J. C. Granados, J. D. Short, and B. K. Banik, Eur. J. Med. Chem., 50, 209 (2012).

    Article  CAS  Google Scholar 

  35. A. Wilson, G. Filzen and G. S. Welmaker, Tetrahedron Lett., 50, 4807 (2009).

    Article  CAS  Google Scholar 

  36. V. Polshettiwar and R. S. Varma, Tetrahedron, 66, 1091 (2010).

    Article  CAS  Google Scholar 

  37. Y. Fang, D. Leysen, and H. C. J. Ottenheijm, Synth. Commun., 25, 1857 (1995).

    Article  CAS  Google Scholar 

  38. Hosseini-Sarvari, E. Sodagar, and M. M. Doroodmand, J. Org. Chem., 76, 2853 (2011).

    Article  CAS  Google Scholar 

  39. Hosseini-Sarvari and E. Safari, J. Sulfur Chem., 32, 463 (2011).

  40. M. Hosseini-Sarvari, E. Safari, A. Jarrahpour, and R. Heiran, C. R. Chim., 15, 980 (2012).

    Article  CAS  Google Scholar 

  41. M. Zarei, A. Jarrahpour, E. Ebrahimi, M. Aye, and S. A. Torabi Badrabady, Tetrahedron, 68, 5505 (2012).

    Article  CAS  Google Scholar 

  42. L. K. Noda, R. M. de Almeida, L. F. D Probst, and N. S. Goncalves, J. Mol. Catal. A: Chem., 225, 39 (2005).

    Google Scholar 

  43. X. Song and A. Sayari, Catal. Rev. Sci. Eng., 38, 329 (1996).

    Article  CAS  Google Scholar 

  44. H.-C. Ma and X.-Z. Jiang, J. Org. Chem., 72, 8943 (2007).

    Article  CAS  Google Scholar 

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Correspondence to M. Hosseini-Sarvari.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1870-1877, December, 2013.

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Hosseini-Sarvari, M., Najafvand-Derikvandi, S., Jarrahpour, A. et al. Nano Sulfated Titania as a Heterogeneous Solid Acid Catalyst for the Synthesis of Pyrroles by Clauson–Kaas Condensation under Solvent-free Conditions. Chem Heterocycl Comp 49, 1732–1739 (2014). https://doi.org/10.1007/s10593-014-1425-3

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  • DOI: https://doi.org/10.1007/s10593-014-1425-3

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