Table of Contents Author Guidelines Submit a Manuscript
The Scientific World Journal
Volume 2012 (2012), Article ID 174784, 8 pages
http://dx.doi.org/10.1100/2012/174784
Research Article

An Efficient Protocol for the Synthesis of Quinoxaline Derivatives at Room Temperature Using Recyclable Alumina-Supported Heteropolyoxometalates

1Cátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de La Plata, Calles 60 y 119, La Plata B1904AAN, Argentina
2Facultad Regional San Nicolás, Universidad Tecnológica Nacional (UTN), Colón N-332, San Nicolás, Buenos Aires 2900, Argentina
3Centro de Investigación y Desarrollo en Ciencias Aplicadas “Dr. J.J. Ronco” (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CCT-CONICET, Calles 47 No. 257, La Plata B1900AJK, Argentina

Received 6 October 2011; Accepted 13 November 2011

Academic Editors: K. Abouzid and H. Amri

Copyright © 2012 Diego M. Ruiz 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. S. D. Undevia, F. Innocenti, J. Ramirez et al., “A phase I and pharmacokinetic study of the quinoxaline antitumour Agent R(+)XK469 in patients with advanced solid tumours,” European Journal of Cancer, vol. 44, no. 12, pp. 1684–1692, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. P. Corona, A. Carta, M. Loriga, G. Vitale, and G. Paglietti, “Synthesis and in vitro antitumor activity of new quinoxaline derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1579–1591, 2009. View at Publisher · View at Google Scholar · View at Scopus
  3. C. Urquiola, D. Gambino, M. Cabrera et al., “New copper-based complexes with quinoxaline N1,N4-dioxide derivatives, potential antitumoral agents,” Journal of Inorganic Biochemistry, vol. 102, no. 1, pp. 119–126, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. Q. Weng, D. Wang, P. Guo et al., “Q39, a novel synthetic Quinoxaline 1,4-Di-N-oxide compound with anti-cancer activity in hypoxia,” European Journal of Pharmacology, vol. 581, no. 3, pp. 262–269, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. S. Wagle, A. V. Adhikari, and N. S. Kumari, “Synthesis of some new 4-styryltetrazolo[1,5-a]quinoxaline and 1-substituted-4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants,” European Journal of Medicinal Chemistry, vol. 44, no. 3, pp. 1135–1143, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. E. Vicente, L. M. Lima, E. Bongard et al., “Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents,” European Journal of Medicinal Chemistry, vol. 43, no. 9, pp. 1903–1910, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. A. Burguete, E. Pontiki, V. D. Hadjipavlou-Litina et al., “Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 23, pp. 6439–6443, 2007. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Budakoti, A. R. Bhat, and A. Azam, “Synthesis of new 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1,3-thiazolino[5,4-b]quinoxaline derivatives and evaluation of their antiamoebic activity,” European Journal of Medicinal Chemistry, vol. 44, no. 3, pp. 1317–1325, 2009. View at Publisher · View at Google Scholar · View at Scopus
  9. W. He, M. R. Myers, B. Hanney et al., “Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: the synthesis and biological activities of RPR127963 an orally bioavailable inhibitor,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 18, pp. 3097–3100, 2003. View at Publisher · View at Google Scholar
  10. Y. B. Kim, Y. H. Kim, J. Y. Park, and S. K. Kim, “Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 2, pp. 541–544, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. J. Y. Jaung, “Synthesis and halochromism of new quinoxaline fluorescent dyes,” Dyes and Pigments, vol. 71, no. 3, pp. 245–250, 2006. View at Publisher · View at Google Scholar · View at Scopus
  12. Q. Y. Zhang, B. K. Liu, W. Q. Chen, Q. Wu, and X. F. Lin, “A green protocol for synthesis of benzo-fused N,S-, N,O- and N,N-heterocycles in water,” Green Chemistry, vol. 10, no. 9, pp. 972–977, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. K. R. J. Thomas, M. Velusamy, T. Lin Jiann, C. H. Chuen, and Y. T. Tao, “Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials,” Chemistry of Materials, vol. 17, no. 7, pp. 1860–1866, 2005. View at Publisher · View at Google Scholar · View at Scopus
  14. M. J. Crossley and L. A. Johnston, “Laterally-extended porphyrin systems incorporating a switchable unit,” Chemical Communications, no. 10, pp. 1122–1123, 2002. View at Google Scholar · View at Scopus
  15. S. Dailey, W. J. Feast, R. J. Peace, I. C. Sage, S. Till, and E. L. Wood, “Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications,” Journal of Materials Chemistry, vol. 11, no. 9, pp. 2238–2243, 2001. View at Publisher · View at Google Scholar · View at Scopus
  16. A. Katoh, T. Yoshida, and J. Ohkanda, “Synthesis of quinoxaline derivatives bearing the styryl and phenylethynyl groups and application to a fluorescence derivatization reagent,” Heterocycles, vol. 52, no. 2, pp. 911–920, 2000. View at Google Scholar · View at Scopus
  17. J. L. Sessler, H. Maeda, T. Mizuno, V. M. Lynch, and H. Furuta, “Quinoxaline-bridged porphyrinoids,” Journal of the American Chemical Society, vol. 124, no. 45, pp. 13474–13479, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. S. A. Raw, C. D. Wilfred, and R. J. K. Taylor, “Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds,” Organic and Biomolecular Chemistry, vol. 2, no. 5, pp. 788–796, 2004. View at Publisher · View at Google Scholar · View at Scopus
  19. D. J. Brown, “Quinoxalines,” in The Chemistry of Heterocyclic Compounds, E. C. Taylor and P. Wipf, Eds., vol. 61, pp. 1–510, John Wiley & Sons, Hoboken, NJ, USA, 2004. View at Google Scholar
  20. S. Antoniotti and E. Duñach, “Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines,” Tetrahedron Letters, vol. 43, no. 22, pp. 3971–3973, 2002. View at Publisher · View at Google Scholar · View at Scopus
  21. N. P. Xekoukoulotakis, C. P. Hadjiantoniou-Maroulis, and A. J. Maroulis, “Synthesis of quinoxalines by cyclization of α-arylimino oximes of α-dicarbonyl compounds,” Tetrahedron Letters, vol. 41, no. 52, pp. 10299–10302, 2000. View at Publisher · View at Google Scholar · View at Scopus
  22. M. R. Islami and Z. Hassani, “One-pot and efficient protocol for synthesis of quinoxaline derivatives,” Arkivoc, vol. 2008, no. 15, pp. 280–287, 2008. View at Google Scholar · View at Scopus
  23. S. V. More, M. N. V. Sastry, C. C. Wang, and Y. Ching-Fa, “Molecular iodine: a powerful catalyst for the easy and efficient synthesis of quinoxalines,” Tetrahedron Letters, vol. 46, no. 37, pp. 6345–6348, 2005. View at Publisher · View at Google Scholar · View at Scopus
  24. M. M. Heravi, S. Taheri, K. Bakhtiari, and H. A. Oskooie, “On water: a practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4· 5H2O,” Catalysis Communications, vol. 8, no. 2, pp. 211–214, 2007. View at Publisher · View at Google Scholar
  25. A. Kumar, S. kumar, A. Saxena, A. De, and S. Mozumdar, “Ni-nanoparticles: an efficient catalyst for the synthesis of quinoxalines,” Catalysis Communications, vol. 9, no. 5, pp. 778–784, 2008. View at Publisher · View at Google Scholar · View at Scopus
  26. J. J. Cai, J. P. Zou, X. Q. Pan, and W. Zhang, “Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives,” Tetrahedron Letters, vol. 49, no. 52, pp. 7386–7390, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. T. K. Huang, R. Wang, L. Shi, and X. X. Lu, “Montmorillonite K-10: an efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water,” Catalysis Communications, vol. 9, no. 6, pp. 1143–1147, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. F. Dong, K. Gong, Z. Fei, X. Zhou, and Z. Liu, “A practical and efficient synthesis of quinoxaline derivatives catalyzed by task-specific ionic liquid,” Catalysis Communications, vol. 9, no. 2, pp. 317–320, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. B. B. F. Mirjalili and A. Akbari, “Nano-TiO2: an eco-friendly alternative for the synthesis of quinoxalines,” Chinese Chemical Letters, vol. 22, no. 6, pp. 753–756, 2011. View at Publisher · View at Google Scholar
  30. B. Krishnakumar, R. Velmurugan, S. Jothivel, and M. Swaminathan, “An efficient protocol for the green synthesis of quinoxaline and dipyridophenazine derivatives at room temperature using sulfated titania,” Catalysis Communications, vol. 11, no. 12, pp. 997–1002, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. M. Jafarpour, A. Rezaeifard, and M. Danehchin, “Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions,” Applied Catalysis A: General, vol. 394, no. 1-2, pp. 48–51, 2011. View at Publisher · View at Google Scholar
  32. R. K. Sharma and C. Sharma, “Zirconium(IV)-modified silica gel: preparation, characterization and catalytic activity in the synthesis of some biologically important molecules,” Catalysis Communications, vol. 12, no. 5, pp. 327–331, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. S. Sadjadi, S. Sadjadi, and R. Hekmatshoar, “Ultrasound-promoted greener synthesis of benzoheterocycle derivatives catalyzed by nanocrystalline copper(II) oxide,” Ultrasonics Sonochemistry, vol. 17, no. 5, pp. 764–767, 2010. View at Publisher · View at Google Scholar · View at Scopus
  34. S. V. More, M. N. V. Sastry, and C. F. Yao, “Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: a simple, proficient and green approach for the synthesis of quinoxalines,” Green Chemistry, vol. 8, no. 1, pp. 91–95, 2006. View at Publisher · View at Google Scholar · View at Scopus
  35. K. T. V. Rao, P. S. S. Prasad, and N. Lingaiah, “Iron exchanged molybdophosphoric acid as an efficient heterogeneous catalyst for the synthesis of quinoxalines,” Journal of Molecular Catalysis A: Chemical, vol. 312, no. 1-2, pp. 65–69, 2009. View at Publisher · View at Google Scholar · View at Scopus
  36. K. Niknam, D. Saberi, and M. Mohagheghnejad, “Silica bonded S-sulfonic acid: a recyclable catalyst for the synthesis of quinoxalines at room temperature,” Molecules, vol. 14, no. 5, pp. 1915–1926, 2009. View at Publisher · View at Google Scholar · View at Scopus
  37. H. R. Darabi, S. Mohandessi, K. Aghapoor, and F. Mohsenzadeh, “A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature,” Catalysis Communications, vol. 8, no. 3, pp. 389–392, 2007. View at Publisher · View at Google Scholar · View at Scopus
  38. S. B. Rajesh, S. R. Swapnil, S. A. Suresh, N. J. Wamanrao, R. B. Sudhakar, and P. P. Rajendra, “An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst,” Tetrahedron Letters, vol. 46, no. 42, pp. 7183–7186, 2005. View at Publisher · View at Google Scholar · View at Scopus
  39. J. F. Zhou, G. X. Gong, K. B. Shi, and S. J. Zhi, “Catalyst-free and solvent-free method for the synthesis of quinoxalines under microwave irradiation,” Chinese Chemical Letters, vol. 20, no. 6, pp. 672–675, 2009. View at Publisher · View at Google Scholar · View at Scopus
  40. M. N. Timofeeva, “Acid catalysis by heteropoly acids,” Applied Catalysis A: General, vol. 256, no. 1-2, pp. 19–35, 2003. View at Publisher · View at Google Scholar · View at Scopus
  41. G. P. Romanelli, D. Bennardi, D. M. Ruiz, G. Baronetti, H. J. Thomas, and J. C. Autino, “A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst,” Tetrahedron Letters, vol. 45, no. 48, pp. 8935–8939, 2004. View at Publisher · View at Google Scholar · View at Scopus
  42. D. O. Bennardi, D. M. Ruiz, G. P. Romanelli, G. T. Baronetti, H. J. Thomas, and J. C. Autino, “Efficient microwave solvent-free synthesis of Flavones, Chromones, Coumarins and Dihydrocoumarins,” Letters in Organic Chemistry, vol. 5, no. 8, pp. 607–615, 2009. View at Publisher · View at Google Scholar · View at Scopus
  43. G. P. Romanelli, D. M. Ruiz, J. C. Autino, and H. E. Giaccio, “A suitable preparation of N-sulfonyl-1,2,3,4 tetrahydroisoquinolines and their ring homologues with a reusable preyssler heteropolyacid as catalyst,” Molecular Diversity, vol. 14, no. 4, pp. 803–807, 2010. View at Publisher · View at Google Scholar
  44. G. Romanelli, P. Vázquez, L. Pizzio et al., “Phenol tetrahydropyranylation catalyzed by silica-alumina supported heteropolyacids with Keggin structure,” Applied Catalysis A: General, vol. 261, no. 2, pp. 163–170, 2004. View at Publisher · View at Google Scholar · View at Scopus
  45. P. Villabrille, G. Romanelli, P. Vázquez, and C. Cáceres, “Vanadium-substituted Keggin heteropolycompounds as catalysts for ecofriendly liquid phase oxidation of 2,6-dimethylphenol to 2,6-dimethyl-1,4- benzoquinone,” Applied Catalysis A: General, vol. 270, no. 1-2, pp. 101–111, 2004. View at Publisher · View at Google Scholar · View at Scopus
  46. P. Villabrille, G. Romanelli, N. Quaranta, and P. Vázquez, “An efficient catalytic route for the preparation of silyl ethers using alumina-supported heteropolyoxometalates,” Applied Catalysis B: Environmental, vol. 96, no. 3-4, pp. 379–386, 2010. View at Publisher · View at Google Scholar · View at Scopus