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Journal of the Iranian Chemical Society

, Volume 11, Issue 2, pp 587–592 | Cite as

Ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane catalyzed by Preyssler acid-mediated nano-TiO2

  • Davood Azarifar
  • Seyed-Mola Khatami
  • Zohreh Najminejad
Original Paper

Abstract

Preyssler-type heteropolyacid supported on TiO2 nanoparticles has been explored as an efficient catalyst in selective oxidation of primary aromatic amines to azoxy derivatives using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as oxidant. The reactions proceeded smoothly under mild and green ultrasound-accelerated conditions to afford the products in high yields. The catalyst recovered from the reaction mixture exhibits long-term stability with no significant drop in its catalytic activity.

Graphical abstract

Keywords

Trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane Nano-TiO2 Preyssler-type heteropolyacid Aromatic amine Azoxy derivative Oxidation 

Notes

Acknowledgments

The authors wish to thank the Research Council of Bu-Ali Sina University and also the Ministry of Science, Research and Technology of Islamic Republic of Iran for financial support to carry out this research.

References

  1. 1.
    M. Gamberini, M.R. Cidade, L.A. Vallota, M.C.S. Armelin, L.C.C. Leite, Carcinogenesis 19, 147–155 (1998)CrossRefGoogle Scholar
  2. 2.
    A.B.E. Vix, P. Muller-Buschbaum, W. Stocker, M. Stamm, J.P. Rabe, Langmuir 16, 10456–10462 (2000)CrossRefGoogle Scholar
  3. 3.
    T. Ikeda, O. Tsutsumi, Science 268, 1873–1875 (1995)CrossRefGoogle Scholar
  4. 4.
    D. Campbell, L.R. Dix, P. Rostron, Dyes Pigm. 29, 77–83 (1995)CrossRefGoogle Scholar
  5. 5.
    J.M. Huang, J.F. Kuo, C.Y.J. Chen, Appl. Polym. Sci. 55, 1217–1229 (1995)CrossRefGoogle Scholar
  6. 6.
    T.L. Gilchrist, in Comprehensive Organic Synthesis, vol. 7, eds. by B. M. Trost, I. Fleming (Pergamon, Oxford, 1991) p. 735Google Scholar
  7. 7.
    D.H. Rosenblatt, E.P. Burrows, in The chemistry of amino, nitroso, and nitro compounds and their derivatives ed. by S. Patai (Wiley, Chichester, 1982) p. 1085Google Scholar
  8. 8.
    S. Sakaue, T. Tsubakino, Y. Nishiyama, Y.J. Ishii, Org. Chem. 58, 3633–3638 (1993)CrossRefGoogle Scholar
  9. 9.
    R.R. Holmes, R.P.J. Bayer, Am. Chem. Soc. 82, 3454–3456 (1960)CrossRefGoogle Scholar
  10. 10.
    F.B. Mallory, K.E. Schueller, C.S.J. Wood, Org. Chem. 26, 3312–3316 (1961)CrossRefGoogle Scholar
  11. 11.
    C.E. Weill, G.S.J. Panson, Org. Chem. 21:803–803 (1956) Google Scholar
  12. 12.
    S. Wada, M. Urano, H.J. Suzuki, Org. Chem. 67, 8254–8257 (2002)CrossRefGoogle Scholar
  13. 13.
    Y. Liu, B. Liu, A. Guo, Z. Dong, S. Jin, Y. Lu, Molecules 16, 3563–3568 (2011)CrossRefGoogle Scholar
  14. 14.
    A. McKillop, R.A. Raphael, E.C. Taylor, J. Org. Chem. 35, 1670–1672 (1970)CrossRefGoogle Scholar
  15. 15.
    J.R. Hwu, A.R. Das, C.W. Yang, J.-J. Huang, M.-H. Hsu, Org. Lett. 7, 3211–3214 (2005)CrossRefGoogle Scholar
  16. 16.
    J.R. Hwu, C.S. Yau, S.-C. Tsay, T.-I. Ho, Tetrahedron Lett. 38, 9001–9004 (1997)CrossRefGoogle Scholar
  17. 17.
    A.R. Becker, L.A.J. Sternson, Org. Chem. 45, 1708–1710 (1980)CrossRefGoogle Scholar
  18. 18.
    N.A. Johnson, E.S.J. Gould, Org. Chem. 39, 407–409 (1974)CrossRefGoogle Scholar
  19. 19.
    Y. Ogata, H. Shimizu, Bull. Chem. Soc. Jpn. 52, 635–636 (1979)CrossRefGoogle Scholar
  20. 20.
    A. Rezaeifard, M. Jafarpour, S. Rayati, R. Shariati, Dyes Pigm. 80, 80–85 (2009)CrossRefGoogle Scholar
  21. 21.
    A. Rezaeifard, M. Jafarpour, M. Naseri, R. Shariati, Dyes Pigm. 76, 840–843 (2008)CrossRefGoogle Scholar
  22. 22.
    F.F. Bamoharram, M.M. Heravi, M. Roshani, M.J. Akbarpour, Mol. Catal. A Chem. 255, 193–198 (2006)CrossRefGoogle Scholar
  23. 23.
    H. Tumma, N. Nagaraju, K.V. Reddy, Appl. Catal. A 353, 54–60 (2009)CrossRefGoogle Scholar
  24. 24.
    A. Nezhadali, M. Akbarpour, Chin. Chem. Lett. 21, 43–46 (2010)CrossRefGoogle Scholar
  25. 25.
    H. Itoh, S. Utamapanya, J.V. Stark, K.J. Klabunde, J.R. Schlup, Chem. Mater. 5, 71–77 (1993)CrossRefGoogle Scholar
  26. 26.
    J. Guzman, B.C. Gates, Nano Lett. 1, 689–692 (2001)CrossRefGoogle Scholar
  27. 27.
    B.M. Choudary, M.L. Kantam, K.V.S. Ranganath, K. Mahendar, B.J. Sreedhar, Am. Chem. Soc. 126, 3396–3397 (2004)CrossRefGoogle Scholar
  28. 28.
    A. Azarifar, R. Nejat-Yami, M. Al-Kobaisi, D.J. Azarifar, Iran. Chem. Soc. 10, 439–446 (2013)CrossRefGoogle Scholar
  29. 29.
    M.A. Fox, M.T. Dulay, Chem. Rev. 93, 341–357 (1993)CrossRefGoogle Scholar
  30. 30.
    S. Anandan, A. Vinu, N. Venkatachalam, B. Arabindoo, V.J. Murugesan, Mol. Catal. A Chem. 256, 312–320 (2006)CrossRefGoogle Scholar
  31. 31.
    M.R. Hoffmann, S.T. Martin, W. Choi, D.W. Bahnemann, Chem. Rev. 95, 69–96 (1995)CrossRefGoogle Scholar
  32. 32.
    M. Rahimizadeh, G. Rajabzadeh, S.-M. Khatami, H. Eshghi, A.J. Shiri, Mol. Catal. A Chem. 323, 59–64 (2010)CrossRefGoogle Scholar
  33. 33.
    D. Azarifar, S.-M. Khatami, M. A. Zolfigol, D. J. Sheikh, Iran. Chem. Soc. doi: 10.1007/s13738-013-0242-4 (2013)
  34. 34.
    D. Azarifar, R. Nejat-Yami, F. Sameri, Z. Akrami, Lett. Org. Chem. 9, 435–439 (2012)CrossRefGoogle Scholar
  35. 35.
    D. Azarifar, D. Sheikh, Helv. Chim. Acta 95, 1217–1225 (2012)CrossRefGoogle Scholar
  36. 36.
    D. Azarifar, D. Sheikh, Chem. Het. Comp. 47, 1128–1136 (2011)CrossRefGoogle Scholar
  37. 37.
    D. Azarifar, K.J. Khosravi, Iran. Chem. Soc. 8, 1006–1013 (2011)CrossRefGoogle Scholar
  38. 38.
    D. Azarifar, K. Khosravi, Eur. J. Chem. 1, 15–19 (2010)CrossRefGoogle Scholar
  39. 39.
    D. Azarifar, K. Khosravi, Synlett. pp. 2755–2758 (2010)Google Scholar
  40. 40.
    D. Azarifar, K. Khosravi, Z. Najminejad, K. Soleimani, Heterocycles 81, 2855–2863 (2010)CrossRefGoogle Scholar
  41. 41.
    D. Azarifar, K. Khosravi, Z. Najminejad, K.J. Soleimani, Iran. Chem. Soc. 9, 321–326 (2012)CrossRefGoogle Scholar
  42. 42.
    D. Azarifar, Z. Najminejad, K. Khosravi, Synth. Commun. 43, 826–836 (2013)CrossRefGoogle Scholar
  43. 43.
    D. Azarifar, Z. Najminejad, K. Khosravi, J. Iran. Chem. Soc. doi: 10.1007/s13738-013-0235-3 (2013)
  44. 44.
    G. Rajabzadeh, A. Jalalian, in Proceedings of the 14th International Sol-gel Conference, Montpellier, France, 2007Google Scholar
  45. 45.
    M.H. Alizadeh, S.P. Harmalker, Y. Jeannin, J. Martin-Frere, M.T.J. Pope, Am. Chem. Soc. 107, 2662–2669 (1985)CrossRefGoogle Scholar
  46. 46.
    S. Suresh, R. Joseph, B. Jayachandran, A.V. Pol, M.P. Vinod, A. Sudalai, H.R. Sonawane, T. Ravindranathan, Tetrahedron 51, 11305–11318 (1995)CrossRefGoogle Scholar
  47. 47.
    H.J. Shine, H.E.J. Mallory, Org. Chem. 27, 2390–2391 (1962)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2013

Authors and Affiliations

  • Davood Azarifar
    • 1
  • Seyed-Mola Khatami
    • 1
  • Zohreh Najminejad
    • 1
  1. 1.Faculty of ChemistryBu-Ali Sina UniversityHamedanIslamic Republic of Iran

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