Advertisement

Journal of the Iranian Chemical Society

, Volume 8, Issue 2, pp 495–501 | Cite as

Ionic liquid 1-(3-Trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes

  • H. Valizadeh
  • M. Amiri
  • A. Shomali
  • F. Hosseinzadeh
Article

Abstract

A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid and subsequent azo-coupling generated the related azo dyes in good to excellent yields at 0–5 °C in short reaction times via a simple experimental procedure.

Keywords

Diazotization Ionic liquid Azo dyes Azo-coupling Diazonium salt 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    K. Gong, D. Fang, H.-L. Wang, X.-L. Zhou, Z.-L. Liu, Dyes Pigments 80 (2009) 30.Google Scholar
  2. [2]
    Z.G. Le, Z.C. Chen, Y. Hu, Q.G. Zheng, Synthesis (2004) 2809.Google Scholar
  3. [3]
    C. Yue, A. Mao, Y. Wei, M. Lü, Catal. Commun. 9 (2008) 1571.Google Scholar
  4. [4]
    L. Wang, H. Li, P. Li, Tetrahedron 65 (2009) 364.Google Scholar
  5. [5]
    D.R. Macfarlane, J.M. Pringle, K.M. Johansson, S.A. Forsyth, M. Forsyth, Chem. Commun. (2006) 1905.Google Scholar
  6. [6]
    C. Paun, J. Barklie, P. Goodrich, H.Q.N. Gunaratne, A. McKeown, V.I. Pârvulescu, C. Hardacre, J. Mol. Catal. A: Chem. 269 (2007) 64.Google Scholar
  7. [7]
    H. Tajik, K. Niknam F. Parsa, J. Iran. Chem. Soc. 6 (2009) 159.CrossRefGoogle Scholar
  8. [8]
    R.S. Bhosale, S.R. Sarda, R.P. Giram, D.S. Raut, S.P. Parwe, S.S. Ardhapure, R.P. Pawar, J. Iran. Chem. Soc. 6 (2009) 519.CrossRefGoogle Scholar
  9. [9]
    A.R. Hajipour, F. Rafiee, A.E. Ruoho, J. Iran. Chem. Soc. 7 (2010) 114.CrossRefGoogle Scholar
  10. [10]
    H. Valizadeh, A. Shockravi, Heteroatom Chem. 20 (2009) 284.Google Scholar
  11. [11]
    H. Valizadeh, H. Gholipour, Synth. Commun. 40 (2010) 1477.Google Scholar
  12. [12]
    H. Valizadeh, Heteroatom Chem. 21 (2010) 78.Google Scholar
  13. [13]
    H. Valizadeh, A. Shockravi, Synth. Commun. 39 (2009) 4341.Google Scholar
  14. [14]
    N. Noroozi-Pesian, J. Khalafy, Z. Malekpoor, Prog. Color Colorants Coat. 2 (2009) 61.Google Scholar
  15. [15]
    H. Zollinger, Color Chemistry-Syntheses, Properties and Applications of Organic Dyes and Pigments, VCH Publishers, New York, 1987, p. 92.Google Scholar
  16. [16]
    T. Okuzumi, E. Nakanishi, T. Tsuji, S. Makino, Tetrahedron Lett. 44 (2003) 5539.Google Scholar
  17. [17]
    H. Dabbagh, A.A. Teimouri, A.N. Chermahini, Dyes Pigments 73 (2007) 239.Google Scholar
  18. [18]
    F. Li, W. Chen, P. Dong, S. Zhang, Biosens. Bioelec. 24 (2009) 2160.Google Scholar
  19. [19]
    D.A. Gorlushko, V.D. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Go, H.Y. Hwang, E.H. Cha, K.-W. 6Chi, Tetrahedron Lett. 49 (2008) 1080.Google Scholar
  20. [20]
    H. Faustino, R.M. El-Shishtawy, L.V. Reis, P.F. Santos, P. Almeida, Tetrahedron Lett. 49 (2008) 6907.Google Scholar
  21. [21]
    D.B. Ramachary, V.V. Narayana, K. Ramakumar, Tetrahedron Lett. 49 (2008) 2704.Google Scholar
  22. [22]
    A. Lyčka, A. Koloničn`y, P. Simůnek, V. Machaček, Dyes Pigments 72 (2007) 208.Google Scholar
  23. [23]
    N. Noroozi-Pesyan, J. Khalafy, Z. Malekpoor, J. Chin. Chem. Soci. 26 (2009) 1018.Google Scholar
  24. [24]
  25. [25]
    K.L. Williamson, Macroscale and Microscale Organic Experiments, 2nd ed., Houghton Mifflin, Boston, 1994.Google Scholar
  26. [26]
    M.J.D. Long, H.J. 6Prochaska, P. Talalay, Med. Sci. 83 (1986) 787.Google Scholar
  27. [27]
    H. Khanmohammadi, M. Darvishpour, Dyes Pigments 81 (2009) 167.Google Scholar
  28. [28]
    H. Dinçalp, F. Toker, İ. Durucasu, N. Avc0ibaş0i, S. Icli, Dyes Pigments 75 (2007) 11.Google Scholar
  29. [29]a)
  30. b).
  31. c).
  32. d).
  33. [30]
    H. Hartmann, I. Zug, J. Chem. Soc. Perkin Trans. 1 (2000) 4316.Google Scholar
  34. [31]
    M. Lutfor R.C. Tschierske, M. Yusoff, S. Silong, Tetrahedron Lett. 46 (2005) 2303.Google Scholar
  35. [32]
    J. Fasihi, Y. Yamini, F. Nourmohammadian, N. Bahramifar, Dyes Pigments 63 (2004) 161.Google Scholar
  36. [33]
    A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, A.C. Najafi, Dyes Pigments 81 (2009) 240.Google Scholar

Copyright information

© Iranian Chemical Society 2011

Authors and Affiliations

  • H. Valizadeh
    • 1
  • M. Amiri
    • 1
  • A. Shomali
    • 1
  • F. Hosseinzadeh
    • 1
  1. 1.Department of Chemistry, Faculty of SciencesAzarbaijan University of Tarbiat MoallemTabrizIran

Personalised recommendations