Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 325268, 5 pages
http://dx.doi.org/10.1155/2013/325268
Research Article

Al(NO3)3 · 9H2O: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Both under Reflux or Solvent-Free Conditions

Department of Chemistry, Semnan University, P.O. Box 35195-363, Semnan, Iran

Received 23 January 2012; Accepted 30 May 2012

Academic Editor: Kotaro Satoh

Copyright © 2013 Eskandar Kolvari and Maryam Mirzaeeyan. 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. P. G. Biginelli, “Ueber aldehyduramide des acetessigäthers. II,” Berichte der Deutschen Chemischen Gesellschaft, vol. 24, no. 2, pp. 2962–2967, 1891. View at Publisher · View at Google Scholar
  2. C. O. Kappe, “Biologically active dihydropyrimidones of the Biginelli-type—a literature survey,” European Journal of Medicinal Chemistry, vol. 35, no. 12, pp. 1043–1052, 2000. View at Publisher · View at Google Scholar
  3. 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 Google Scholar · View at Scopus
  4. K. Folkers, H. J. Harwood, and J. Johnson, “Hydrogenation of cyclic ureides under elevated temperatures and pressures. I.1 2-Keto-1,2,3,4-tetrahydropyrimidines,” Journal of the American Chemical Society, vol. 56, no. 5, pp. 1180–1185, 1934. View at Publisher · View at Google Scholar
  5. I. T. Phucho, A. Nongpiur, S. Tumtin, R. Nongrum, and R. L. Nongkhlaw, “Recent progress in the chemistry of dihydropyrimidinones,” Rasayan Journal of Chemistry, vol. 2, no. 3, pp. 662–676, 2009. View at Google Scholar · View at Scopus
  6. A. Saini, S. Kumar, and J. S. Sandhu, “Biginelli reaction,” Journal of the Indian Chemical Society, vol. 84, no. 10, pp. 959–970, 2007. View at Google Scholar · View at Scopus
  7. 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
  8. 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
  9. A. Studer, P. Jeger, P. Wipf, and D. P. Curran, “Fluorous synthesis: fluorous protocols for the ugi and Biginelli multicomponent condensations,” Journal of Organic Chemistry, vol. 62, no. 9, pp. 2917–2924, 1997. View at Google Scholar · View at Scopus
  10. E. H. Hu, D. R. Sidler, and U.-H. Dolling, “Note unprecedented catalytic three component one-pot condensation reaction:  an efficient synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones,” The Journal of Organic Chemistry, vol. 63, no. 10, pp. 3454–3457, 1998. View at Publisher · View at Google Scholar
  11. 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
  12. J. C. Rodríguez-Domínguez, 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 · View at Scopus
  13. K. S. De and R. A. Gibbs, “Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 3,4Dihydropyrimidin2(1H)ones,” Synthetic Communications, vol. 35, no. 20, pp. 2645–2651, 2005. View at Publisher · View at Google Scholar
  14. M. G. Kulkarni, S. W. Chavhan, M. P. Shinde et al., “Zeolite catalyzed solvent-free one-pot synthesis of dihydropyrimidin-2(1H)- ones—a practical synthesis of monastrol,” Beilstein Journal of Organic Chemistry, vol. 5, article 4, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. V. Radha Rani, N. Srinivas, M. Radha Kishan, S. J. Kulkarni, and K. V. Raghavan, “Zeolite-catalyzed cyclocondensation reaction for the selective synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Green Chemistry, vol. 3, no. 6, pp. 305–306, 2001. View at Publisher · View at Google Scholar · View at Scopus
  16. M. Tajbakhsh, B. Mohajerani, M. M. Heravi, and A. N. Ahmadi, “Natural HEU type zeolite catalyzed Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H) one derivatives,” Journal of Molecular Catalysis A, vol. 236, no. 1-2, pp. 216–219, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. I. Cepanec, M. Litvić, M. Filipan-Litvić, and I. Grüngold, “Antimony(III) chloride-catalysed Biginelli reaction: a versatile method for the synthesis of dihydropyrimidinones through a different reaction mechanism,” Tetrahedron, vol. 63, no. 48, pp. 11822–11827, 2007. View at Publisher · View at Google Scholar · View at Scopus
  18. F. Xu, J. J. Wang, and Y. P. Tian, “New procedure for one pot synthesis of 3,4 dihydropyrimidin 2(1H) ones by Biginelli reaction,” Synthetic Communications, vol. 38, no. 8, pp. 1299–1310, 2008. View at Publisher · View at Google Scholar
  19. F. Shirini, M. A. Zolfigol, and E. Mollarazi, “Solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones using trichloroisocyanuric acid,” Letters in Organic Chemistry, vol. 2, no. 8, pp. 718–720, 2005. View at Publisher · View at Google Scholar · View at Scopus
  20. S. K. De and R. A. Gibbs, “Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4- dihydropyrimidin-2-(1H)-ones under solvent-free conditions,” Synthesis, no. 11, pp. 1748–1750, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. P. Salehi, M. Dabiri, M. A. Zolfigol, and M. A. Bodaghi Fard, “Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Tetrahedron Letters, vol. 44, no. 14, pp. 2889–2891, 2003. View at Publisher · View at Google Scholar · View at Scopus
  22. S. F. Hojati, M. Gholizadeh, M. Haghdoust, and F. Shafiezadeh, “1,3-dichloro-5,5-dimethylhydantoin as a novel and efficient homogeneous catalyst in Biginelli reaction,” Bulletin of the Korean Chemical Society, vol. 31, no. 11, pp. 3238–3240, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. M. A. Zolfigol, P. Salehi, A. Ghaderi, and M. Shiri, “A catalytic and green procedure for Friedlander quinoline synthesis in aqueous media,” Catalysis Communications, vol. 8, no. 8, pp. 1214–1218, 2007. View at Publisher · View at Google Scholar · View at Scopus
  24. M. A. Zolfigol and M. Safaiee, “Synthesis of 1,4-dihydropyridines under solvent-free conditions,” Synlett, no. 5, pp. 827–828, 2004. View at Google Scholar · View at Scopus
  25. A. Khazaei, M. A. Zolfigol, E. Kolvari, N. Koukabi, H. Soltani, and L. S. Bayani, “Electrophilic bromination of alkenes, alkynes, and aromatic amines with iodic acid/potassium bromide under mild conditions,” Synthetic Communications, vol. 40, no. 19, pp. 2954–2962, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. M. A. Zolfigol, P. Salehi, M. Shiri, and Z. Tanbakouchian, “A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media,” Catalysis Communications, vol. 8, no. 2, pp. 173–178, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. A. Dondoni, A. Massi, and S. Sabbatini, “Improved synthesis and preparative scale resolution of racemic monastrol,” Tetrahedron Letters, vol. 43, no. 34, pp. 5913–5916, 2002. View at Publisher · View at Google Scholar · View at Scopus
  28. S. D. Salim and K. G. kamanchi, “Sulfated tungstate: an alternative, eco-friendly catalyst for Biginelli reaction,” Catalysis Communications, vol. 12, no. 12, pp. 1153–1156, 2011. View at Publisher · View at Google Scholar
  29. M. Zeinali-Dastmalbaf, A. Davoodnia, M. M. Heravi, N. Tavakoli-Hoseini, A. Khojastehnezhad, and H. A. Zamani, “Silica gel-supported polyphosphoric acid (PPA-SiO2) catalyzed one-pot multi-component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and—thiones: an efficient method for the Biginelli reaction,” Bulletin of the Korean Chemical Society, vol. 32, no. 2, pp. 656–658, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. H. A. Oskooie, M. M. Heravi, N. Karimi, and M. H. Monjezy, “FeCl3 immobilized in Al-MCM 41: an efficient catalyst system for the Biginelli reaction,” Synthetic Communications, vol. 41, no. 6, pp. 826–831, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. A. R. Hajipour, L. Khazdooz, and A. Zarei, “Brønsted acidic ionic liquid-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions,” Synthetic Communications, vol. 41, no. 15, pp. 2200–2208, 2011. View at Publisher · View at Google Scholar · View at Scopus
  32. O. Rosati, M. Curini, F. Montanari, M. Nocchetti, and S. Genovese, “α-zirconium sulfophenylphosphonate as a catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent free conditions,” Catalysis Letters, vol. 141, no. 6, pp. 850–853, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. 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
  34. C. O. Kappe, “A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate,” The Journal of Organic Chemistry, vol. 62, no. 21, pp. 7201–7204, 1997. View at Publisher · View at Google Scholar