Chemistry of Heterocyclic Compounds

, Volume 49, Issue 3, pp 457–465 | Cite as

Synthesis and absorption abilities of pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes

  • F. Karcı
  • F. Karcı

A series of 13 novel pyrazolo[5,1-c][1,2,4]triazine-based disperse dyes was synthesized by heating ethyl pyrazolylhydrazonocyanoacetate in glacial acetic acid. Solvent and acid-base influences on the wavelength of maximum absorption have been studied.


ethyl cyanoacetate pyrazole diazo coupling reaction intramolecular cyclization solvatochromism 


  1. 1.
    F. Freeman, Synthesis, 925 (1981).Google Scholar
  2. 2.
    Y. Tominaga, Y. Honkawa, M. Hara, and A. Hosomi, J. Heterocycl. Chem., 27, 775 (1990).CrossRefGoogle Scholar
  3. 3.
    U. Hanefeld, C. W. Rees, A. J. P. White, and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 13, 1545 (1996).CrossRefGoogle Scholar
  4. 4.
    A. G. A. Elagamey and F. M. A.-A. El-Taweel, J. Prakt. Chem., 333, 333 (1991).CrossRefGoogle Scholar
  5. 5.
    F. M. A. Latif, M. A. Barsy, E. A. Elrady, and M. Hassan, J. Chem. Res., Synop., 12, 696 (1999).CrossRefGoogle Scholar
  6. 6.
    K. Senga, T. Novinson, R. H. Springer, R. P. Rao, D. E. O’Brien, R. K. Robins, and H. R. Wilson, J. Med. Chem., 18, 312 (1975).CrossRefGoogle Scholar
  7. 7.
    S. P. Singh and D. Kumar, Heterocycles, 31, 855 (1990).CrossRefGoogle Scholar
  8. 8.
    L. H. Sternbach, Prog. Drug Res., 22, 229 (1978).Google Scholar
  9. 9.
    N. Jaiswal, R. Jaiswal, J. Barthwal, and K. Kishor, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 20B, 252 (1981).Google Scholar
  10. 10.
    S. G. Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A. C. Ekinci, and A. Vidin, Eur. J. Med. Chem., 35, 761 (2000).CrossRefGoogle Scholar
  11. 11.
    L. R. S. Dias, M. J. Alvim, A. C. C. Freitas, E. J. Barreiro, and A. L. P. Miranda, Pharm. Acta Helv., 69, 163 (1994).CrossRefGoogle Scholar
  12. 12.
    J. W. Lyga, R. M. Patera, M. J. Plummer, B. P. Halling, and D. A. Yuhas, Pestic. Sci., 42, 29 (1994).CrossRefGoogle Scholar
  13. 13.
    M. J. Genin, C. Biles, B. J. Keiser, S. M. Poppe, S. M. Swaney, W. G. Tarpley, Y. Yagi, and D. L. Romero, J. Med. Chem., 43, 1034 (2000).CrossRefGoogle Scholar
  14. 14.
    N. Ertan, Dyes Pigm., 44, 41 (2000).CrossRefGoogle Scholar
  15. 15.
    A. K. Khalil, M. A. Hassan, M. M. Mohamed, and A. M. El-Sayed, Dyes Pigm., 66, 241 (2005).CrossRefGoogle Scholar
  16. 16.
    A. Emandi, I. Serban, and R. Bandula, Dyes Pigm., 41, 63 (1999).CrossRefGoogle Scholar
  17. 17.
    P. C. Tsai and I. J. Wang, Dyes Pigm., 64, 259 (2005).CrossRefGoogle Scholar
  18. 18.
    Y. W. Ho, Dyes Pigm., 64, 223 (2005).CrossRefGoogle Scholar
  19. 19.
    F. Karcı, N. Şener, M. Yamaç, İ. Şener, and A. Demirçalı, Dyes Pigm., 80, 47 (2009).CrossRefGoogle Scholar
  20. 20.
    E. E. Oruc, B. Kocyigit-Kaymakcioglu, B. Oral, H.Z. Altunbas-Toklu, L. Kabasakal, and S. Rollas, Arch. Pharm., 339, 267 (2006).CrossRefGoogle Scholar
  21. 21.
    S. S. Kandil, F. I. Abdel-Hay, and R. M. Issa, J. Therm. Anal. Calorim., 63, 173 (2001).CrossRefGoogle Scholar
  22. 22.
    S. A. Abdel-Latif, Synth. React. Inorg. Met.-Org. Chem., 31, 1355 (2001).Google Scholar
  23. 23.
    M. V. Partridge and M. F. G. Stevens, J. Chem. Soc. C, 1127 (1966).Google Scholar
  24. 24.
    E. J. Gray, M. F. G. Stevens, G. Tennant, and R. J. S. Vevers, J. Chem. Soc., Perkin Trans. 1, 14, 1496 (1976).CrossRefGoogle Scholar
  25. 25.
    M. H. Elnagdi, M. R. H. El-Moghayar, D. H. Fleita, E. A. A. Hafez, and S. M. Fahmy, J. Org. Chem., 41, 3781 (1976).CrossRefGoogle Scholar
  26. 26.
    M. H. Elnagdi, M. R. H. Elmoghayar, E. M. Kandeel, and M. K. A. Ibrahim, J. Heterocycl. Chem., 14, 227 (1977).CrossRefGoogle Scholar
  27. 27.
    M. H. Elnagdi, E. M. Zayed, M. A. E. Khalifa, and S. A. Ghozlan, Monatsh. Chem., 112, 245 (1981).CrossRefGoogle Scholar
  28. 28.
    H. A. Hammouda, A. A. El-Barbary, and M. A. F. Sharaf, J. Heterocycl. Chem., 21, 945 (1984).CrossRefGoogle Scholar
  29. 29.
    K. U. Sadek, M. A. Selim, and M. A. El-Maghraby, J. Chem. Eng. Data, 30, 514 (1985).CrossRefGoogle Scholar
  30. 30.
    A. A. El-Agamey, M. R. H. El-Moghayar, and M. H. Elnagdi, Pharmazie, 40, 176 (1985).Google Scholar
  31. 31.
    M. M. Girges, M. A. Hanna, and A. A. Fadda, Chem. Pap., 47, 186 (1993).Google Scholar
  32. 32.
    A. M. Farag, K. M. Dawood, and Z. E. Kandeel, Tetrahedron, 52, 7893 (1996).CrossRefGoogle Scholar
  33. 33.
    F. Karcı, İ. Şener, A. Demirçalı, and N. Burukoğlu, Color. Technol., 122, 264 (2006).CrossRefGoogle Scholar
  34. 34.
    F. Karcı and F. Karcı, Dyes Pigm., 76, 97 (2008).CrossRefGoogle Scholar
  35. 35.
    F. Karcı, Color. Technol., 121, 275 (2005).CrossRefGoogle Scholar
  36. 36.
    M. A. Metwally, E. Abdel-Latif, A. M. Khalil, F. A. Amer, and G. Kaupp, Dyes Pigm., 62, 181 (2004).CrossRefGoogle Scholar
  37. 37.
    H. Joshi, F. S. Kamounah, G. Van Der Zwan, C. Gooijer, and L. Antonov, J. Chem. Soc., Perkin Trans 2, 2303 (2001).Google Scholar
  38. 38.
    F. Karcı, A. Demirçalı, İ. Şener, and T. Tilki, Dyes Pigm., 71, 90 (2006).CrossRefGoogle Scholar
  39. 39.
    F. Karcı and A. Demirçalı, Dyes Pigm., 71, 97 (2006).CrossRefGoogle Scholar
  40. 40.
    F. Karcı and A. Demirçalı, Dyes Pigm., 74, 288 (2007).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.Pamukkale University, Faculty of Science-ArtsDenizliTurkey
  2. 2.Pamukkale University, Higher Vocational School of DenizliDenizliTurkey

Personalised recommendations