Table of Contents
ISRN Organic Chemistry
Volume 2013, Article ID 706437, 13 pages
http://dx.doi.org/10.1155/2013/706437
Research Article

Three Component Reaction: An Efficient Synthesis and Reactions of 3,4-Dihydropyrimidin-2(1H)-Ones and Thiones Using New Natural Catalyst

Department of Chemistry, Faculty of Science, South Valley University, Qena 83523, Egypt

Received 28 May 2013; Accepted 1 July 2013

Academic Editors: S. Bellemin-Laponnaz, D. K. Chand, T. C. Dinadayalane, and J. Wu

Copyright © 2013 A. M. Elmaghraby 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. E. W. Hurst and R. Hull, “Two new synthetic substances active against viruses of the psittacosis-lymphogranuloma- trachoma group,” Journal of Medicinal Chemistry, vol. 3, no. 2, pp. 215–229, 1961. View at Publisher · View at Google Scholar
  2. M. Ashok, B. S. Holla, and N. S. Kumari, “Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities,” European Journal of Medicinal Chemistry, vol. 42, no. 3, pp. 380–385, 2007. View at Publisher · View at Google Scholar
  3. S. S. Bahekar and D. B. Shinde, “Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid derivatives,” Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 7, pp. 1733–1736, 2004. View at Publisher · View at Google Scholar
  4. T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, and T. J. Mitchison, “Smart molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen,” Science, vol. 286, no. 5441, pp. 971–974, 1999. View at Publisher · View at Google Scholar · View at Scopus
  5. C. O. Kappe, “Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog,” Accounts of Chemical Research, vol. 33, no. 12, pp. 879–888, 2000. View at Publisher · View at Google Scholar
  6. A. D. Patil, N. V. Kumar, W. C. Kokke et al., “Novel alkaloids from the sponge Batzella sp.: inhibitors of HIV gp120-human CD4 binding,” Journal of Organic Chemistry, vol. 60, no. 5, pp. 1182–1188, 1995. View at Google Scholar · View at Scopus
  7. B. B. Snider, J. Chen, A. D. Patil, and A. J. Freyer, “Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D,” Tetrahedron Letters, vol. 37, no. 39, pp. 6977–6980, 1996. View at Publisher · View at Google Scholar · View at Scopus
  8. P. Biginelli, “Derivati aldeidureidici degli eteri acetil-ed ossalacetico,” Gazzetta Chimica Italiana, vol. 23, pp. 360–416, 1893. View at Google Scholar
  9. P. Wipf and A. Cunningham, “A solid phase protocol of the Biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry,” Tetrahedron Letters, vol. 36, no. 43, pp. 7819–7822, 1995. View at Publisher · View at Google Scholar · View at Scopus
  10. C. O. Kappe, “100 years of the Biginelli dihydropyrimidine synthesis,” Tetrahedron, vol. 49, no. 32, pp. 6937–6963, 1993. View at Publisher · View at Google Scholar · View at Scopus
  11. D. Dallinger, A. Stadler, and C. O. Kappe, “Solid- and solution-phase synthesis of bioactive dihydropyrimidines,” Pure and Applied Chemistry, vol. 76, no. 5, pp. 1017–1024, 2004. View at Google Scholar · View at Scopus
  12. C. O. Kappe, “4-aryldihydropyrimidines via the Biginelli condensation: aza-analogs of nifedipine-type calcium channel modulators,” Molecules, vol. 3, no. 1, pp. 1–9, 1998. View at Publisher · View at Google Scholar
  13. C. O. Kappe and A. Stadler, “The Biginelli dihydropyrimidine synthesis,” Organic Reactions, vol. 63, pp. 1–116, 2004. View at Google Scholar
  14. C. Simon, T. Constantieux, and J. Rodriguez, “Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions,” European Journal of Organic Chemistry, no. 24, pp. 4957–4980, 2004. View at Publisher · View at Google Scholar · View at Scopus
  15. C. O. Kappe, “The generation of dihydropyrimidine libraries utilizing Biginelli multicomponent chemistry,” QSAR and Combinatorial Science, vol. 22, no. 6, pp. 630–645, 2003. View at Google Scholar · View at Scopus
  16. H. E. Zaugg and W. B. Martin, “α-amidoalkylations at carbon,” in Organic Reactions, vol. 14, pp. 88–90, John Wiley & Sons, New York, NY, USA, 1965. View at Publisher · View at Google Scholar
  17. C. O. Kappe, “The Biginelli reaction,” in Multicomponent Reactions, pp. 95–120, John Wiley & Sons, New York, NY, USA, 2005. View at Google Scholar
  18. L. Z. Gong, X. H. Chen, and X. Y. Xu, “Asymmetric organocatalytic biginelli reactions: a new approach to quickly access optically active 3,4-dihydropyrimidin-2-(1H)-ones,” Chemistry—A European Journal, vol. 13, no. 32, pp. 8920–8926, 2007. View at Publisher · View at Google Scholar
  19. A. Dondoni and A. Massi, “Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction,” Tetrahedron Letters, vol. 42, no. 45, pp. 7975–7978, 2001. View at Publisher · View at Google Scholar · View at Scopus
  20. A. Shaabani and A. Bazgir, “Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions,” Tetrahedron Letters, vol. 45, no. 12, pp. 2575–2577, 2004. View at Publisher · View at Google Scholar · View at Scopus
  21. B. J. Ahn, M. S. Gang, K. Chae, Y. Oh, J. Shin, and W. Chalg, “A microwave-assisted synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones catalyzed by FeCl3-supported Nanopore Silica under solvent-free conditions,” Journal of Industrial and Engineering Chemistry, vol. 14, no. 3, pp. 401–405, 2008. View at Publisher · View at Google Scholar
  22. X. Zhang, Y. Li, C. Liu, and J. Wang, “An efficient synthesis of 4-substituted pyrazolyl-3,4-dihydropyrimidin-2(1H)-(thio)ones catalyzed by Mg(ClO4)2 under ultrasound irradiation,” Journal of Molecular Catalysis A, vol. 253, no. 1-2, pp. 207–211, 2006. View at Publisher · View at Google Scholar
  23. J. T. Li, J. F. Han, J. H. Yang, and T. S. Li, “An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation,” Ultrasonics Sonochemistry, vol. 10, no. 3, pp. 119–122, 2003. View at Publisher · View at Google Scholar
  24. N. Foroughifar, A. Mobinikhaledi, and H. Fathinejad Jirandehi, “Synthesis of some biginelli compounds in solvent medium using a photochemistry method,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 178, no. 3, pp. 495–500, 2003. View at Publisher · View at Google Scholar · View at Scopus
  25. E. H. Hu, D. R. Sidler, and U. H. Dolling, “Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin- 2(1H)-ones,” Journal of Organic Chemistry, vol. 63, no. 10, pp. 3454–3457, 1998. View at Publisher · View at Google Scholar
  26. C. V. Reddy, M. Mahesh, P. V. K. Raju, T. R. Babu, and V. V. N. Reddy, “Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Tetrahedron Letters, vol. 43, no. 14, pp. 2657–2659, 2002. View at Publisher · View at Google Scholar · View at Scopus
  27. A. Kumar and R. A. Maurya, “An efficient bakers' yeast catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-ones,” Tetrahedron Letters, vol. 48, no. 26, pp. 4569–4571, 2007. View at Publisher · View at Google Scholar · View at Scopus
  28. Y. Q. Zhang, C. Wang, G. S. Li, J. C. Li, H. M. Liu, and Q. H. Wu, “One-pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Expandable Graphite,” Chinese Journal of Organic Chemistry, vol. 25, pp. 1265–1267, 2005. View at Google Scholar
  29. R. V. Yarapathi, S. Kurva, and S. Tammishetti, “Synthesis of 3,4-dihydropyrimidin-2(1H)ones using reusable poly(4-vinylpyridine-co-divinylbenzene)-Cu(II)complex,” Catalysis Communications, vol. 5, no. 9, pp. 511–513, 2004. View at Publisher · View at Google Scholar · View at Scopus
  30. J. Azizian, A. A. Mohammadi, A. R. Karimi, and M. R. Mohammadizadeh, “KAl(SO4)2·12H2O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction: one-pot synthesis of di-hydropyrimidinones under solvent-free conditions,” Applied Catalysis A, vol. 300, no. 1, pp. 85–88, 2006. View at Publisher · View at Google Scholar
  31. N. Mizuno and M. Misono, “Heterogeneous catalysis,” Chemical Reviews, vol. 98, no. 1, pp. 199–217, 1998. View at Google Scholar · View at Scopus
  32. A. A. Bakibaev and V. D. Filimonov, “Synthesis of hydrogenated acridine-1,8-diones & 1,4-dihydropyrimidines by reaction of urea with 1,3-dicarbonyl compounds,” Russian Journal of Organic Chemistry, vol. 27, pp. 854–859, 1991. View at Google Scholar
  33. Y. Yu, D. Liu, C. Liu, and G. Luo, “One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst,” Bioorganic & Medicinal Chemistry Letters, vol. 17, no. 12, pp. 3508–3510, 2007. View at Publisher · View at Google Scholar
  34. A. S. Paraskar, G. K. Dewkar, and A. Sudalai, “Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Tetrahedron Letters, vol. 44, no. 16, pp. 3305–3308, 2003. View at Publisher · View at Google Scholar · View at Scopus
  35. M. Gohain, D. Prajapati, and S. Sandhub, “A novel Cu-catalysed three-component one-pot synthesis of dihydropyrimidin-2(1H)-ones using microwaves under solvent free conditions,” Synlett, p. 235, 2004. View at Google Scholar
  36. Y. Ma, C. Qian, L. Wang, and M. Yang, “Lanthanide triflate catalyzed Biginelli reaction. one-pot synthesis of dihydropyrimidinones under solvent-free conditions,” The Journal of Organic Chemistry, vol. 65, no. 12, pp. 3864–3868, 2000. View at Publisher · View at Google Scholar
  37. V. T. Kamble, D. B. Muley, S. T. Atkore, and S. D. Dakore, “Three component reaction: an efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones using heterogeneous catalyst,” Chinese Journal of Chemistry, vol. 28, no. 3, pp. 388–392, 2010. View at Publisher · View at Google Scholar · View at Scopus
  38. B. Gangadasu, S. Palaniappan, and V. J. Rao, “One-pot synthesis of dihydropyrimidinones using polyaniline-bismoclite complex. A facile and reusable catalyst for the biginelli reaction,” Synlett, no. 7, pp. 1285–1287, 2004. View at Google Scholar · View at Scopus
  39. A. K. Mitra and K. Banerjee, “Clay catalysed synthesis of dihydropyrimidinones under solvent-free conditions,” Synlett, no. 10, pp. 1509–1511, 2003. View at Google Scholar · View at Scopus
  40. J. Mabry and B. Ganem, “Studies on the Biginelli reaction: a mild and selective route to 3,4-dihydropyrimidin-2(1H)-ones via enamine intermediates,” Tetrahedron Letters, vol. 47, no. 1, pp. 55–56, 2006. View at Publisher · View at Google Scholar
  41. T. Ghorge, R. Tahilramani, and D. V. Mehta, “Condensed heterocycles from 5-ethoxycarbonyl-6-methyltetrahydropyrimidin-2-ones,” Communications, pp. 405–407, 1975. View at Google Scholar
  42. N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, and C. Peppe, “Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction,” Tetrahedron, vol. 58, no. 24, pp. 4801–4807, 2002. View at Publisher · View at Google Scholar · View at Scopus
  43. J. S. Yadav, B. V. S. Reddy, P. Sridhar et al., “Green protocol for the biginelli three-component reaction: Ag 3PW12O40 as a novel, water-tolerant heteropolyacid for the synthesis of 3,4-dihydropyrimidinones,” European Journal of Organic Chemistry, no. 3, pp. 552–557, 2004. View at Google Scholar · View at Scopus
  44. K. Folkers and T. B. Johnson, “Researches on pyrimidines. CXXXVI. The mechanism of formation of tetrahydropyrimidines by the Biginelli reaction,” Journal of the American Chemical Society, vol. 55, no. 9, pp. 3784–3791, 1933. View at Google Scholar · View at Scopus
  45. R. D. Carlos, D. Bernardi, and G. Kirsch, “ZrCl4 or ZrOCl2 under neat conditions: optimized green alternatives for the Biginelli reaction,” Tetrahedron Letters, vol. 48, no. 33, pp. 5777–5780, 2007. View at Publisher · View at Google Scholar
  46. N. Foroughifar, A. Mobinikhaledi, H. F. Jirandehi, and S. Memar, “Microwave-assisted synthesis of some BI- and tricyclic pyrimidine derivatives,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 178, no. 6, pp. 1269–1276, 2003. View at Publisher · View at Google Scholar · View at Scopus
  47. B. Ahmed, R. A. Khan, Habibullah, and M. Keshari, “An improved synthesis of Biginelli-type compounds via phase-transfer catalysis,” Tetrahedron Letters, vol. 50, no. 24, pp. 2889–2892, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. E. Ramu, V. Kotra, N. Bansal, R. Varala, and S. R. Adapa, “Green approach for the efficient synthesis of Biginelli compounds promoted by citric acid under solvent-free conditions,” RASĀYAN Journal of Chemistry, vol. 1, no. 1, pp. 188–194, 2008. View at Google Scholar