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The Scientific World Journal
Volume 2013, Article ID 543768, 4 pages
http://dx.doi.org/10.1155/2013/543768
Research Article

A Simple and Green Procedure for the Synthesis of 5-Arylidenerhodanines Catalyzed by Diammonium Hydrogen Phosphate in Water

Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission and Ministry of Education, College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan, Hubei 430074, China

Received 13 August 2013; Accepted 10 September 2013

Academic Editors: C. Aragoncillo and N. Zohreh

Copyright © 2013 Liangliang Han 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. Sortino, P. Delgado, S. Juárez et al., “Synthesis and antifungal activity of (Z)-5-arylidenerhodanines,” Bioorganic & Medicinal Chemistry, vol. 15, no. 1, pp. 484–494, 2007. View at Publisher · View at Google Scholar · View at Scopus
  2. Y. Momose, K. Meguro, H. Ikeda, C. Hatanaka, S. Oi, and T. Sohda, “Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds,” Chemical and Pharmaceutical Bulletin, vol. 39, no. 6, pp. 1440–1445, 1991. View at Google Scholar · View at Scopus
  3. J. H. Ahn, S. J. Kim, W. S. Park et al., “Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 11, pp. 2996–2999, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. O. Zvarec, S. W. Polyak, W. Tieu et al., “5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 8, pp. 2720–2722, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. M. J. Robertson, G. Hadzic, J. Ambrus et al., “The rhodadyns, a new class of small molecule inhibitors of dynamin GTPase activity,” ACS Medicinal Chemistry Letters, vol. 3, no. 5, pp. 352–356, 2012. View at Google Scholar
  6. N. Zidar, T. Tomašić, R. Šink et al., “Discovery of novel 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2, 4-dione inhibitors of MurD ligase,” Journal of Medicinal Chemistry, vol. 53, no. 18, pp. 6584–6594, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. N. Zidar, T. Tomašić, R. Šink et al., “New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: design, synthesis, crystal structures, and biological evaluation,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5512–5523, 2011. View at Publisher · View at Google Scholar · View at Scopus
  8. M. Song, C. Zheng, X. Deng et al., “Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents,” European Journal of Medicinal Chemistry, vol. 54, pp. 403–412, 2012. View at Google Scholar
  9. S. Kamila, H. Ankati, and E. R. Biehl, “An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors,” Tetrahedron Letters, vol. 52, no. 34, pp. 4375–4377, 2011. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Kamila, H. Ankati, E. Harry, and E. R. Biehl, “A facile synthesis of novel 3-(aryl/alkyl-2-ylmethyl)-2-thioxothiazolidin-4-ones using microwave heating,” Tetrahedron Letters, vol. 53, no. 17, pp. 2195–2198, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. V. Opletalova, J. Dolezel, K. Kralova, M. Pesko, J. Kunes, and J. Jampilek, “Synthesis and characterization of (Z)-5-arylmethylidenerhodanines with photosynthesis-inhibiting properties,” Molecules, vol. 16, no. 6, pp. 5207–5227, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. X.-Z. Lian, Y.-Q. Li, and M.-Y. Zhou, “Ionic liquid/H2O system promoted condensation of aromatic aldehydes and rhodanine,” Chinese Journal of Organic Chemistry, vol. 26, no. 9, pp. 1272–1274, 2006. View at Google Scholar · View at Scopus
  13. H. Li, J. Yang, S. Ma, and C. Qiao, “Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein,” Bioorganic & Medicinal Chemistry, vol. 20, no. 14, pp. 4194–4200, 2012. View at Google Scholar
  14. J.-F. Zhou, Y.-Z. Song, F.-X. Zhu, and Y.-L. Zhu, “Facile synthesis of 5-benzylidene rhodamine derivatives under microwave irradiation,” Synthetic Communications, vol. 36, no. 22, pp. 3297–3303, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. B.-Y. Yang and D.-H. Yang, “Solvent-free synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones catalysed by glycine under microwave irradiation,” Journal of Chemical Research, vol. 35, no. 4, pp. 238–239, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. N. H. Metwally, N. M. Rateb, and H. F. Zohdi, “A simple and green procedure for the synthesis of 5-arylidene-4-thiazolidinones by grinding,” Green Chemistry Letters and Reviews, vol. 4, no. 3, pp. 225–228, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. D. Hardej, C. R. Ashby Jr., N. S. Khadtare, S. S. Kulkarni, S. Singh, and T. T. Talele, “The synthesis of phenylalanine-derived C5-substituted rhodanines and their activity against selected methicillin-resistant Staphylococcus aureus (MRSA) strains,” European Journal of Medicinal Chemistry, vol. 45, no. 12, pp. 5827–5832, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. K. Gong, Z.-W. He, Y. Xu, D. Fang, and Z.-L. Liu, “Green synthesis of 5-benzylidene rhodanine derivatives catalyzed by 1-butyl-3-methyl imidazolium hydroxide in water,” Monatshefte für Chemie, vol. 139, no. 8, pp. 913–915, 2008. View at Publisher · View at Google Scholar · View at Scopus
  19. J.-J. Ma, S.-T. Gao, Z. Li et al., “Synthesis of 5-arylmethylidene-2-thio-4-thiazolidinone derivatives catalyzed by alkaline ionic liquid,” Chinese Journal of Organic Chemistry, vol. 28, no. 2, pp. 339–342, 2008. View at Google Scholar · View at Scopus
  20. J. F. Zhou, F. X. Zhu, Y. Z. Song, and Y. L. Zhu, “Synthesis of 5-arylalkylidenerhodanines catalyzed by tetrabutylammonium bromine in water under microwave irradiation,” ARKIVOC, vol. 2006, no. 14, pp. 175–180, 2006. View at Publisher · View at Google Scholar
  21. M. Zhang, C. D. Wang, S. L. Yu, Z. B. Tian, and L. Zhang, “The condensation of rhodanine or N-phenylrhodanine with aromatic aldehyde under microwave, solid base as a supporter,” Chemical Journal of Chinese Universities, vol. 15, no. 11, pp. 1647–1650, 1994. View at Google Scholar
  22. C.-J. Li and L. Chen, “Organic chemistry in water,” Chemical Society Reviews, vol. 35, no. 1, pp. 68–82, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. A. Chanda and V. V. Fokin, “Organic synthesis “on water”,” Chemical Reviews, vol. 109, no. 2, pp. 725–748, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. R. N. Butler and A. G. Coyne, “Water: nature's reaction enforcer-comparative effects for organic synthesis “in-water” and “on-water”,” Chemical Reviews, vol. 110, no. 10, pp. 6302–6337, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, and P. Salehi, “Diammonium hydrogen phosphate: an efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media,” Synthetic Communications, vol. 37, no. 7, pp. 1097–1108, 2007. View at Publisher · View at Google Scholar · View at Scopus
  26. S. Balalaie, S. Abdolmohammadi, H. R. Bijanzadeh, and A. M. Amani, “Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media,” Molecular Diversity, vol. 12, no. 2, pp. 85–91, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. F. Darviche, S. Balalaie, F. Chadegani, and P. Salehi, “Diammonium hydrogen phosphate as a neutral and efficient catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives in aqueous media,” Synthetic Communications, vol. 37, no. 7, pp. 1059–1066, 2007. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Dabiri, P. Salehi, M. Baghbanzadeh, Y. Vakilzadeh, and S. Kiani, “Diammonium hydrogen phosphate as an efficient and inexpensive catalyst for the synthesis of bis(indolyl)methanes under solvent-free conditions,” Monatshefte fur Chemie, vol. 138, no. 6, pp. 595–597, 2007. View at Publisher · View at Google Scholar · View at Scopus
  29. H. Huo, Z. Zhou, A. Zhang, and L. Wu, “Ruthenium(II)-catalyzed transfer hydrogenation of aldehydes with new water-soluble monotosylated ethylenediamines as ligands,” Research on Chemical Intermediates, vol. 38, no. 1, pp. 261–268, 2012. View at Publisher · View at Google Scholar · View at Scopus
  30. Z. Zhou and Q. Ma, “Polyethylene glycol-bound Ru catalyst for asymmetric transfer hydrogenation of aromatic ketones in water,” Applied Organometallic Chemistry, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. Z. Zhou and Y. Sun, “Water-soluble chiral aminosulfonamides as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation,” Catalysis Communications, vol. 10, no. 13, pp. 1685–1688, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. Z. Zhou and L. Wu, “Proline-based amino amide hydrochlorides as ligands for asymmetric transfer hydrogenation of prochiral ketones in water,” Catalysis Communications, vol. 9, no. 15, pp. 2539–2542, 2008. View at Publisher · View at Google Scholar · View at Scopus