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Journal of Chemistry
Volume 2013 (2013), Article ID 308419, 5 pages
http://dx.doi.org/10.1155/2013/308419
Research Article

Diphenyl (4′-(Aryldiazenyl)biphenyl-4-ylamino)(pyridin-3-yl)methylphosphonates as Azo Disperse Dyes for Dyeing Polyester Fabrics

1Department of Chemistry, Faculty of Science, University of Tanta, Tanta 31527, Egypt
2School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK

Received 17 June 2012; Accepted 23 August 2012

Academic Editor: Ana Cristi Basile Dias

Copyright © 2013 Mohamed F. Abdel-Megeed et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. M. Ordóñez, H. Rojas-Cabrera, and C. Cativiela, “An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives,” Tetrahedron, vol. 65, no. 1, pp. 17–49, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Ordóňez, F. J. Sayago, and C. Cativiela, “Synthesis of quaternary α-aminophosphonic acids,” Tetrahedron, vol. 68, no. 32, pp. 6369–6412, 2012. View at Publisher · View at Google Scholar
  3. R. Hirschmann, A. B. Smith, C. M. Taylor et al., “Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids,” Science, vol. 265, no. 5169, pp. 234–237, 1994. View at Google Scholar · View at Scopus
  4. C. B. Reddy, K. S. Kumar, M. A. Kumar et al., “PEG-SO3H catalyzed synthesis and cytotoxicity of a-aminophosphonates,” European Journal of Medicinal Chemistry, vol. 47, pp. 553–559, 2012. View at Google Scholar
  5. C. Li, B. Song, K. Yan et al., “One pot synthesis of α-aminophosphonates containing bromo and 3,4,5-trimethoxybenzyl groups under solvent-free conditions,” Molecules, vol. 12, no. 2, pp. 163–172, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. G. S. Prasad, J. R. Krishna, M. Manjunath et al., “Synthesis, NMR, X-ray crystallography and bioactivity of some α-aminophosphonates,” Arkivoc, vol. 13, pp. 133–141, 2007. View at Google Scholar · View at Scopus
  7. D. Y. Hu, Q. Q. Wan, S. Yang et al., “Synthesis and antiviral activities of amide derivatives containing the α-aminophosphonate moiety,” Journal of Agricultural and Food Chemistry, vol. 56, no. 3, pp. 998–1001, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. E. D. Naydenova, P. T. Todorov, M. N. Topashka-Ancheva et al., “Novel N-(phosphonomethyl) glycine derivatives: design, characterization and biological activity,” European Journal of Medicinal Chemistry, vol. 43, no. 6, pp. 1199–1205, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. L. Tušek-Božić, M. Juribašić, P. Traldi, V. Scarcia, and A. Furlani, “Synthesis, characterization and antitumor activity of palladium(II) complexes of monoethyl 8-quinolylmethylphosphonate,” Polyhedron, vol. 27, no. 4, pp. 1317–1328, 2008. View at Publisher · View at Google Scholar · View at Scopus
  10. B. Wang, Z. W. Miao, J. Wang, R. Y. Chen, and X. D. Zhang, “Synthesis and biological evaluation of novel naphthoquinone fused cyclic aminoalkylphosphonates and aminoalkylphosphonic monoester,” Amino Acids, vol. 35, no. 2, pp. 463–468, 2008. View at Publisher · View at Google Scholar · View at Scopus
  11. E. D. Naydenova, P. T. Todorov, P. I. Mateeva, R. N. Zamfirova, N. D. Pavlov, and S. B. Todorov, “Synthesis and biological activity of novel small peptides with aminophosphonates moiety as NOP receptor ligands,” Amino Acids, vol. 39, no. 5, pp. 1537–1543, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. N. Oniţa, I. Şişu, M. Penescu, V. L. Purcarea, and L. Kurunczi, “Synthesis, characterization and biological activity of some α-aminophosphonates,” Farmacia, vol. 58, no. 5, pp. 531–545, 2010. View at Google Scholar · View at Scopus
  13. X. Zhang, Y. Qu, X. Fan et al., “Solvent-free synthesis of pyrimidine nucleoside-aminophosphonate hybrids and their biological activity evaluation,” Nucleosides, Nucleotides and Nucleic Acids, vol. 29, no. 8, pp. 616–627, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. J.-Z. Liu, B.-A. Song, H.-T. Fan et al., “Synthesis and in vitro study of pseudo-peptide thioureas containing α-aminophosphonate moiety as potential antitumor agents,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 5108–5112, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. J. Liu, S. Yang, X. Li et al., “Synthesis and antiviral bioactivity of chiral thioureas containing leucine and phosphonate moieties,” Molecules, vol. 15, no. 8, pp. 5112–5123, 2010. View at Publisher · View at Google Scholar · View at Scopus
  16. C. Caldés, B. Vilanova, M. Adrover, F. Muñoz, and J. Donoso, “Understanding non-enzymatic aminophospholipid glycation and its inhibition. Polar head features affect the kinetics of Schiff base formation,” Bioorganic and Medicinal Chemistry, vol. 19, no. 15, pp. 4536–4543, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. I. El Sayed, S. M. El Kosy, M. A. Hawata, A. A. El Gokha, A. Tolan, and M. M. Abd El-Sattar, “One-pot synthesis of novel α-aminophosphonate derivatives containing a pyrazole moiety,” American Journal of Science, vol. 7, pp. 357–361, 2011. View at Google Scholar
  18. A. Pandey, P. Singh, and L. Iyengar, “Bacterial decolorization and degradation of azo dyes,” International Biodeterioration and Biodegradation, vol. 59, no. 2, pp. 73–84, 2007. View at Publisher · View at Google Scholar · View at Scopus
  19. K. Smith, G. A. El-Hiti, and A. Hamilton, “Unexpected formation of substituted anilides via reactions of trifluoroacetanilides with lithium reagents,” Journal of the Chemical Society, Perkin Transactions 1, no. 24, pp. 4041–4042, 1998. View at Google Scholar · View at Scopus
  20. K. Smith, G. A. El-Hiti, and A. P. Shukla, “Variation in site of lithiation with ring substituent of N-aryl-N,N-dimethylureas: application in synthesis,” Journal of the Chemical Society, Perkin Transactions 1, no. 16, pp. 2305–2313, 1999. View at Google Scholar · View at Scopus
  21. K. Smith, G. A. El-Hiti, and A. S. Hegazy, “Unexpected variations in sites of lithiation of N-(2-methoxybenzyl)- pivalamide,” Synlett, no. 14, pp. 2242–2244, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. K. Smith, G. A. El-Hiti, A. S. Hegazy, A. Fekri, and B. M. Kariuki, “Variation in sites of lithiation of substituted N-benzylpivalamides and N-benzyl-N, N-dimethylureas: application in synthesis,” Arkivoc, vol. 14, pp. 266–300, 2009. View at Google Scholar · View at Scopus
  23. K. Smith, G. A. El-Hiti, M. A. Abdo, and M. F. Abdel-Megeed, “Regiospecific electrophilic substitution of aminoquinazolinones: directed lithiation of 3-(pivaloylamino)- and 3-(acetylamino)-2-methylquinazolin-4(3H)- ones,” Journal of the Chemical Society, Perkin Transactions 1, no. 8, pp. 1029–1033, 1995. View at Google Scholar · View at Scopus
  24. K. Smith, G. A. El-Hiti, M. F. Abdel-Megeed, and M. A. Abdo, “Lithiation of 3-(acylammo)-2-unsubstituted-, 3-(acylamino)-2-ethyl-, and 3-(acylamino)-2-propyl-4(3H)-quinazolinones: convenient syntheses of more complex quinazolinones,” Journal of Organic Chemistry, vol. 61, no. 2, pp. 647–655, 1996. View at Google Scholar · View at Scopus
  25. K. Smith, G. A. El-Hiti, M. F. Abdel-Megeed, and M. A. Abdo, “Lithiation of 2-alkyl-3-amino- and 2-alkyl-3-(methylamino)-4(3H)-quinazolinones,” Journal of Organic Chemistry, vol. 61, no. 2, pp. 656–661, 1996. View at Publisher · View at Google Scholar · View at Scopus
  26. K. Smith, G. A. El-Hiti, and S. A. Mahgoub, “Lithiation and side-chain substitution of 3-alkyl-1H-quinoxalin-2-ones,” Synthesis, no. 15, pp. 2345–2348, 2003. View at Google Scholar · View at Scopus
  27. K. Smith, G. A. El-Hiti, and A. C. Hawes, “Carbonylation of doubly lithiated N-aryl-N,N-dimethylureas: a novel approach to isatins via intramolecular trapping of acyllithiums,” Synthesis, no. 13, pp. 2047–2052, 2003. View at Google Scholar · View at Scopus
  28. G. A. El-Hiti, “A convenient procedure for the synthesis of novel modified 3-substituted 1H-quinoxaline-2-thiones via side-chain lithiation of 3-alkyl-1H-quinoxaline-2-thiones,” Synthesis, no. 18, pp. 2799–2804, 2003. View at Google Scholar · View at Scopus
  29. G. A. El-Hiti, “A convenient procedure for the formation of 2-substituted thiazolopyridines,” Monatshefte fur Chemie, vol. 134, no. 6, pp. 837–841, 2003. View at Publisher · View at Google Scholar · View at Scopus
  30. G. A. El-Hiti, “A simple procedure for the side-chain lithiation of 2-alkyl-3H-quinazoline-4-thiones: application in synthesis,” Synthesis, no. 3, pp. 363–368, 2004. View at Google Scholar · View at Scopus
  31. G. A. El-Hiti, “Application of organolithium in organic synthesis: a simple and convenient procedure for the synthesis of more complex 6-substituted 3H-quinazolin-4-ones,” Monatshefte fur Chemie, vol. 135, no. 3, pp. 323–331, 2004. View at Publisher · View at Google Scholar · View at Scopus
  32. K. Smith, G. A. El-Hiti, and M. F. Abdel-Megeed, “Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)- ones: application in synthesis,” Synthesis, no. 13, pp. 2121–2130, 2004. View at Publisher · View at Google Scholar · View at Scopus
  33. K. Smith, G. A. El-Hiti, and A. S. Hegazy, “A simple and convenient procedure for lithiation and side-chain substitution of 2-alkyl-4-(methylthio)quinazolines and 2-alkyl-4- methoxyquinazolines,” Synthesis, no. 17, pp. 2951–2961, 2005. View at Publisher · View at Google Scholar · View at Scopus
  34. K. Smith, G. A. El-Hiti, and A. S. Hegazy, “Lateral lithiation of N-(2-methylbenzyl)-N,N-dimethylurea and N-(2-methylbenzyl)-pivalamide: synthesis of tetrahydroisoquinolines,” Synthesis, no. 8, pp. 1371–1380, 2010. View at Publisher · View at Google Scholar · View at Scopus
  35. K. Smith, G. A. El-Hiti, A. S. Hegazy, and A. Fekri, “A simple and convenient high yielding synthesis of substituted isoindolines,” Heterocycles, vol. 80, no. 2, pp. 941–956, 2010. View at Publisher · View at Google Scholar · View at Scopus
  36. K. Smith, G. A. El-Hiti, and A. S. Hegazy, “One-pot synthesis of substituted isoindolin-1-ones via lithiation and substitution of N-benzyl-N,N-dimethylureas,” Chemical Communications, vol. 46, no. 16, pp. 2790–2792, 2010. View at Publisher · View at Google Scholar · View at Scopus
  37. K. Smith, G. A. El-Hiti, A. S. Hegazy, and B. Kariuki, “Simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N-benzyl-N,N-dimethylureas,” Beilstein Journal of Organic Chemistry, vol. 7, pp. 1219–1227, 2011. View at Google Scholar
  38. K. A. Browne, D. D. Deheyn, G. A. El-Hiti, K. Smith, and I. Weeks, “Simultaneous quantification of multiple nucleic acid targets using chemiluminescent probes,” Journal of the American Chemical Society, vol. 133, no. 37, pp. 14637–14648, 2011. View at Publisher · View at Google Scholar
  39. M. F. Abdel-Megeed, M. M. Azaam, and G. A. El-Hiti, “3-Arylazo-2-thioxo-2,3-dihydro-1H-quinazolin-4-ones as azodisperse dyes for dyeing polyester fabrics,” Monatshefte fur Chemie, vol. 138, no. 2, pp. 153–156, 2007. View at Publisher · View at Google Scholar · View at Scopus
  40. Anon, Standard Methods for the Determination of the Color Fastness of Textiles and Leather, Society of Dyes and Colorists, Bradford, UK, 5th edition, 1990.