Table of Contents
Organic Chemistry International
Volume 2013, Article ID 512074, 5 pages
http://dx.doi.org/10.1155/2013/512074
Research Article

An Efficient and Green Method for Synthesis of 2,4,5-Triarylimidazoles without Use of Any Solvent, Catalyst, or Solid Surface

Department of Chemistry, Jadavpur University, Kolkata 700 032, India

Received 31 August 2013; Accepted 31 October 2013

Academic Editor: Jason Belitsky

Copyright © 2013 Swati Samanta 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. L. Weber, “The application of multi-component reactions in drug discovery,” Current Medicinal Chemistry, vol. 9, no. 23, pp. 2085–2093, 2002. View at Google Scholar · View at Scopus
  2. C. Hulme and V. Gore, “Multi-component reactions: emerging chemistry in drug discovery ‘from Xylocain to Crixivan’,” Current Medicinal Chemistry, vol. 10, no. 1, pp. 51–80, 2003. View at Publisher · View at Google Scholar · View at Scopus
  3. P. A. Tempest, “Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction,” Current Opinion in Drug Discovery and Development, vol. 8, no. 6, pp. 776–788, 2005. View at Google Scholar · View at Scopus
  4. A. Dömling, “Recent developments in isocyanide based multicomponent reactions in applied chemistry,” Chemical Reviews, vol. 106, no. 1, pp. 17–89, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. D. M. D'Souza and T. J. J. Müller, “Multi-component syntheses of heterocycles by transition-metal catalysis,” Chemical Society Reviews, vol. 36, no. 7, pp. 1095–1108, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. M. D. S. Duque, A. Christophe, N. Isambert, T. Constantieux, and J. Rodriguez, “β-diketo building blocks for MCRs-based syntheses of heterocycles,” Topics in Heterocyclic Chemistry, vol. 23, pp. 227–277, 2010. View at Publisher · View at Google Scholar
  7. N. J. Liverton, J. W. Butcher, C. F. Claiborne et al., “Design and synthesis of potent, selective, and orally bioavailable tetrasubstituted imidazole inhibitors of p38 mitogen-activated protein kinase,” Journal of Medicinal Chemistry, vol. 42, no. 12, pp. 2180–2190, 1999. View at Publisher · View at Google Scholar · View at Scopus
  8. A. K. Takle, M. J. B. Brown, S. Davies et al., “The identification of potent and selective imidazole-based inhibitors of B-Raf kinase,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 2, pp. 378–381, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. S. E. de Laszlo, C. Hacker, B. Li et al., “Potent, orally absorbed glucagon receptor antagonists,” Bioorganic and Medicinal Chemistry Letters, vol. 9, no. 5, pp. 641–646, 1999. View at Publisher · View at Google Scholar · View at Scopus
  10. T. Maier, R. Schmierer, K. Bauer, H. Bieringer, H. Buerstell, and B. Sachse, “1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides,” US Patent 4820335, 1989.
  11. R. Liebl, R. Handte, H. Mildenberger, K. Bauer, and H. Bieringer, “Preparation of 1-phenyl-2-imidazolidinones and -2-imidazolidinethiones as herbicides,” German Offen. DE 3, 604, 042, 1987, Chemical Abstracts, vol. 108, 6018g, 1988.
  12. L. Wang, K. W. Woods, Q. Li et al., “Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure—activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation,” Journal of Medicinal Chemistry, vol. 45, no. 8, pp. 1697–1711, 2002. View at Publisher · View at Google Scholar · View at Scopus
  13. T. F. Gallagher, S. M. Fier-Thompson, R. S. Garigipati et al., “2,4,5-triarylimidazole inhibitors of IL-1 biosynthesis,” Bioorganic and Medicinal Chemistry Letters, vol. 5, no. 11, pp. 1171–1176, 1995. View at Publisher · View at Google Scholar · View at Scopus
  14. J. G. Lombardino and E. H. Wiseman, “Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles,” Journal of Medicinal Chemistry, vol. 17, no. 11, pp. 1182–1188, 1974. View at Google Scholar · View at Scopus
  15. R. A. Turner, C. F. Huebner, and C. R. Scholz, “Studies on imidazole compounds. I. 4-Methylimidazole and related compounds,” Journal of the American Chemical Society, vol. 71, no. 8, pp. 2801–2803, 1949. View at Google Scholar · View at Scopus
  16. A. R. Khosropour, “Ultrasound-promoted greener synthesis of 2,4,5-trisubstituted imidazoles catalyzed by Zr(acac)4 under ambient conditions,” Ultrasonics Sonochemistry, vol. 15, no. 5, pp. 659–664, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. J. N. Sangshetti, N. D. Kokare, S. A. Kotharkara, and D. B. Shinde, “Ceric ammonium nitrate catalysed three component one-pot efficient synthesis of 2,4,5-triaryl-1H-imidazoles,” Journal of Chemical Sciences, vol. 120, no. 5, pp. 463–467, 2008. View at Publisher · View at Google Scholar · View at Scopus
  18. B. Karami, K. Eskandari, and A. Ghasemi, “Facile and rapid synthesis of some novel polysubstituted imidazoles by employing magnetic Fe3O4 nanoparticles as a high efficient catalyst,” Turkish Journal of Chemistry, vol. 36, pp. 601–614, 2012. View at Google Scholar
  19. M. G. Shen, C. Cai, and W. B. Yi, “Ytterbium perfluorooctanesulfonate as an efficient and recoverable catalyst for the synthesis of trisubstituted imidazoles,” Journal of Fluorine Chemistry, vol. 129, no. 6, pp. 541–544, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. L. M. Wang, Y. H. Wang, H. Tian, Y. F. Yao, J. H. Shao, and B. Liu, “Ytterbium triflate as an efficient catalyst for one-pot synthesis of substituted imidazoles through three-component condensation of benzil, aldehydes and ammonium acetate,” Journal of Fluorine Chemistry, vol. 127, no. 12, pp. 1570–1573, 2006. View at Publisher · View at Google Scholar · View at Scopus
  21. S. D. Jadhav, N. D. Kokare, and S. D. Jadhav, “Phosphomolybdic acid catalyzed facile one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil and aromatic aldehydes,” Journal of Heterocyclic Chemistry, vol. 45, no. 5, pp. 1461–1464, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. L. Wang and C. Cai, “Polymer-supported zinc chloride: a highly active and reusable heterogeneous catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles,” Monatshefte fur Chemie, vol. 140, no. 5, pp. 541–546, 2009. View at Publisher · View at Google Scholar · View at Scopus
  23. G. V. M. Sharma, Y. Jyothi, and P. S. Lakshmi, “Efficient room-temperature synthesis of tri- and tetrasubstituted imidazoles catalyzed by ZrCl4,” Synthetic Communications, vol. 36, no. 20, pp. 2991–3000, 2006. View at Publisher · View at Google Scholar · View at Scopus
  24. K. Vikrant and M. Ritu, “Synthesis of substituted imidazoles via a multi-component condensation catalyzed by p-toluene sulfonic acid, PTSA,” Research Journal of Chemical Sciences, vol. 2, no. 4, pp. 18–23, 2012. View at Google Scholar
  25. G. Brahmachari and S. Das, “A Simple and straightforward method for one-pot synthesis of 2,4,5-triarylimidazoles using titanium dioxide as an ecofriendly and recyclable catalyst under solvent free conditions,” Indian Journal of Chemistry, vol. 52, no. 3, pp. 387–393, 2013. View at Google Scholar
  26. S. Mashkouri and M. R. Naimi-Jamal, “Mechanochemical solvent-free and catalyst-free one-pot synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones with quantitative yields,” Molecules, vol. 14, no. 1, pp. 474–479, 2009. View at Publisher · View at Google Scholar · View at Scopus
  27. P. Galletti, M. Pori, and D. Giacomini, “Catalyst-free Strecker reaction in water: a simple and efficient protocol using acetone cyanohydrin as cyanide source,” European Journal of Organic Chemistry, no. 20-21, pp. 3896–3903, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. S. V. Nalage, M. B. Kalyankar, V. S. Patil, S. V. Bhosale, S. U. Deshmukh, and R. P. Pawar, “An efficient noncatalytic protocol for the synthesis of trisubstituted imidazole in polyethylene glycol using microwaves,” Open Catalysis Journal, vol. 3, no. 1, pp. 58–61, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. K. F. Shelke, S. B. Sapkal, S. S. Sonar, B. R. Madje, B. B. Shingate, and M. S. Shingare, “An efficient synthesis of 2,4,5-triaryl-1H-imidazole derivatives catalyzed by boric acid in aqueous media under ultrasound-irradiation,” Bulletin of the Korean Chemical Society, vol. 30, no. 5, pp. 1057–1060, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. V. S. V. Satyanarayana and A. Sivakumar, “An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2·6H2O under heterogeneous conditions,” Chemical Papers, vol. 65, no. 4, pp. 519–526, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. A. Parveen, M. R. S. Ahmed, K. A. Shaikh, S. P. Deshmukh, and R. P. Pawar, “Efficient synthesis of 2,4,5-triaryl substituted imidazoles under solvent free conditions at room temperature,” Arkivoc, vol. 2007, no. 16, pp. 12–18, 2007. View at Google Scholar · View at Scopus
  32. J. F. Zhou, G. X. Gong, X. J. Sun, and Y. L. Zhu, “Facile method for one-step synthesis of 2,4,5-triarylimidazoles under catalyst-free, solvent-free, and microwave-irradiation conditions,” Synthetic Communications, vol. 40, no. 8, pp. 1134–1141, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. S. Samai, G. C. Nandi, P. Singh, and M. S. Singh, “L-proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles,” Tetrahedron, vol. 65, no. 49, pp. 10155–10161, 2009. View at Publisher · View at Google Scholar · View at Scopus