Browse > Article
http://dx.doi.org/10.5012/jkcs.2010.54.6.737

Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives  

Rizk, Hala F. (Department of Chemistry, Faculty of Science, Tanta University)
El-Badawi, Mahmoud A. (Department of Chemistry, Faculty of Science, Tanta University)
Ibrahim, Seham A. (Department of Chemistry, Faculty of Science, Tanta University)
El-Borai, Mohamed A. (Department of Chemistry, Faculty of Science, Tanta University)
Publication Information
Journal of the Korean Chemical Society / v.54, no.6, 2010 , pp. 737-743 More about this Journal
Abstract
Coupling of 5-amino-1,3-diaryl-pyrazoles 1a-c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l. Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso- 1H-pyrazoles 2a-c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a-l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l. and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1H-pyrazoles 1a-c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o-aminoazo compounds 5a-f. Cyclisation of compounds 5a-f in pyridine and cupric acetate gave the corresponding triazoles 6a-f. The coupling of compounds 6a-f with different aryl diazonium salts gave compounds 7a-j. The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.
Keywords
Pyrazolo[4,3-d]-1,2,3-triazoles; $\"{o}$-Aminoazo compounds; Fluorescent properties; Fastness properties;
Citations & Related Records

Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Rangnekar, D. W.; Dhamnaskar, S. V. J. Heterocycl. Chem. 1988, 25, 1663.   DOI
2 Vicentini, C.; Manfredini, S.; Manfrini, M.; Bazzanini, R.; Musiu, C.; Putzolu, M.; Perra, G.; Marongiu, M. E. Archiv der pharmazie. 1998, 331, 269.   DOI
3 Benjamam, E. B.; Srivastava, A.; Coburn, K. R.; Faulkner, A. L.; Seibel, W. L. Tetrahedron Lett. 2003, 44, 3009.   DOI
4 Rangnekar, D. V.; Dhamnaskar, S. V. J. Heterocyclic. Chem. 1988, 25, 1.   DOI
5 Rangnekar, D. W.; Tagdiwala, P. V. Dyes and Pigments. 1986, 7, 289.   DOI
6 Rizk, H. F.; El-Badawi, M. A.; Ibrahim, S. A.; El-Borai, M. A. Arab. J. Chem. 2010, 4, xx.
7 Rizk, H. F;. El-Badawi, M. A.; Ibrahim, S. A.; El-Borai, M. A. Org. Chem. An. indian J. 2008, 4, 115.
8 Anon Standard Methods for the Determination of the Color Fastness of Textiles and Leather, 5th edn, Society of Dyes and Colorists Publication, Bradford, England, 1990.
9 Ho, Y. W. Dyes and Pigments 2005, 64, 223.   DOI
10 Bazgir, A.; Khanaposhtani, M.; Maryam, M.; Soorki, A. A. Bioorg. Med. Chem. Lett. 2008, 18, 5800.   DOI
11 Dias, L. R. S.; Alvim, M. J; Freitas, A. C. C.; Barreiro, E. J.; Miranda, A. L. P. Pharmaceutica Acta Helvetiae 1994, 69, 163.   DOI
12 Karci, F.; Demircah, A. Dyes and Pigments 2006, 71, 97.   DOI
13 El-Kashef, H. S.; El-Emary, T. I.; Gasquet, M.; Timon-David, P.; Maldonado, J.; Vanelle, P. Pharmazie. 2000, 55, 572.
14 El-Emary, T. I.; Al-Muaikel, N.; Moustafa, O. S. Phosphorus, Sulfur, Silicon 2001, 177, 195.
15 Abramov, A. M.; Ceulemans, E.; Jacker, C.; Auweraer, M. V.; Dehaen, W. Tetrahedron 2001, 57, 9123.   DOI
16 Quiroga, J.; Cruz, S.; Nogueras, M. J. Heterocycl. Chem. 2001, 38, 53.   DOI
17 Wu, Y.-C.; Chen, Y.-J.; Li, H.-J.; Zou, X.-M.; Hu, F.-Z.; Yang, H.-Z. J. Fluorine Chem. 2006, 127, 409.   DOI
18 El-Emary, T. I. J. Chin. Chem. Soc. 2006, 533, 91.