Table of Contents
ISRN Organic Chemistry
Volume 2012, Article ID 480989, 8 pages
http://dx.doi.org/10.5402/2012/480989
Research Article

An Efficient One-Pot Green Protocol for the Synthesis of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-Ones Using Recyclable Amberlyst 15 DRY as a Heterogeneous Catalyst via Three-Component Biginelli-Like Reaction

Laboratory of Heterocycles, School of Studies in Chemistry & Biochemistry, Vikram University, Ujjain 456010, Madhya Pradesh, India

Received 2 September 2012; Accepted 24 September 2012

Academic Editors: J. M. Campagne and A. Hajra

Copyright © 2012 Srinivasa Rao Jetti 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. J. H. Clark, Ed., Catalysis of Organic Reactions by Supported Reagents, VCH Publishers, New York, NY, USA, 1994.
  2. R. A. Sheldon and H. Van Bekkum, Catalysis through Heterogeneous Catalysis, Wiely-VCH, Weinheim, Germany, 2002.
  3. G. D. Yadav and M. S. Krishnan, “An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol,” Organic Process Research & Development, vol. 2, no. 2, pp. 86–95, 1998. View at Google Scholar · View at Scopus
  4. G. D. Yadav and P. K. Goel, “Selective synthesis of perfumery grade cyclohexyl esters from cyclohexene and carboxylic acids over ion exchange resins: an example of 100% atom economy,” Green Chemistry, vol. 2, no. 2, pp. 71–78, 2000. View at Google Scholar · View at Scopus
  5. S. M. Mahajani and M. M. Sharma, “Reaction of glyoxal with aliphatic alcohols using cationic exchange resins as catalysts,” Organic Process Research and Development, vol. 1, no. 2, pp. 97–105, 1997. View at Google Scholar · View at Scopus
  6. A. K. Kolah, S. M. Mahajani, and M. M. Sharma, “Acetalization of formaldehyde with methanol in batch and continuous reactive distillation columns,” Industrial and Engineering Chemistry Research, vol. 35, no. 10, pp. 3707–3720, 1996. View at Google Scholar · View at Scopus
  7. G. D. Yadav and A. V. Joshi, “A green route for the acylation of resorcinol with acetic acid,” Clean Technologies and Environmental Policy, vol. 4, no. 3, pp. 157–164, 2002. View at Publisher · View at Google Scholar
  8. S. B. Patil, R. P. Bhat, and S. D. Samant, “Cation-exchange resins: efficient heterogeneous catalysts for facile synthesis of dibenzoxanthene from β-naphthol and aldehydes,” Synthetic Communications, vol. 36, no. 15, pp. 2163–2168, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. C. O. Kappe, “Dipolar cycloaddition reactions of dihydropyrimidine-fused mesomeric betaines: an approach toward conformationally restricted dihydropyrimidine derivatives,” Journal of Organic Chemistry, vol. 62, no. 10, pp. 3109–3118, 1997. View at Google Scholar · View at Scopus
  10. F. Bossert and W. Vater, “1,4-Dihydropyridines—a basis for developing new drugs,” Medicinal Research Reviews, vol. 9, no. 3, pp. 291–324, 1989. View at Publisher · View at Google Scholar · View at Scopus
  11. K. S. Atwal, G. C. Rovnyak, J. Schwartz et al., “Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines,” Journal of Medicinal Chemistry, vol. 33, no. 5, pp. 1510–1515, 1990. View at Google Scholar · View at Scopus
  12. K. Folkers and T. B. Johnson, “Researches on pyrimidines. CXXXIII. Some reactions and derivatives of 2-keto-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine,” Journal of the American Chemical Society, vol. 55, no. 7, pp. 2886–2893, 1933. View at Google Scholar · View at Scopus
  13. 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 · View at Scopus
  14. J. Lu, Y. Bai, Z. Wang, B. Yang, and H. Ma, “One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst,” Tetrahedron Letters, vol. 41, no. 47, pp. 9075–9078, 2000. View at Google Scholar · View at Scopus
  15. D. S. Bose, L. Fatima, and H. B. Mereyala, “Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction: comparison of ethanol, water, and solvent-free conditions,” Journal of Organic Chemistry, vol. 68, no. 2, pp. 587–590, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. B. C. Ranu, A. Hajra, and U. Jana, “Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction,” Journal of Organic Chemistry, vol. 65, no. 19, pp. 6270–6272, 2000. View at Publisher · View at Google Scholar · View at Scopus
  17. E. Rafiee and H. Jafari, “A practical and green approach towards synthesis of dihydropyrimidinones: using heteropoly acids as efficient catalysts,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 9, pp. 2463–2466, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. K. Ramalinga, P. Vijayalakshmi, and T. N. B. Kaimal, “Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction,” Synlett, no. 6, pp. 863–865, 2001. View at Google Scholar · View at Scopus
  19. 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
  20. J.-P. Wan and Y.-J. Pan, “Chemo-/regioselective synthesis of 6-unsubstituted dihydropyrimidinones, 1,3-thiazines and chromones via novel variants of Biginelli reaction,” Chemical Communications, no. 19, pp. 2768–2770, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. J. S. Yadav, B. V. Subba Reddy, R. Srinivas, C. Venugopal, and T. Ramalingam, “LiClO4-catalyzed one-pot synthesis of dihydropyrimidinones: an improved protocol for Biginelli reaction,” Synthesis, no. 9, pp. 1341–1345, 2001. View at Google Scholar · View at Scopus
  22. G. Maiti, P. Kundu, and C. Guin, “One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: an improved procedure for the Biginelli reaction,” Tetrahedron Letters, vol. 44, no. 13, pp. 2757–2758, 2003. View at Publisher · View at Google Scholar · View at Scopus
  23. 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
  24. M. M. Abelman, S. C. Smith, and D. R. James, “Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses,” Tetrahedron Letters, vol. 44, no. 24, pp. 4559–4562, 2003. View at Publisher · View at Google Scholar · View at Scopus
  25. J. Lu and H. Ma, “Iron(III)-catalyzed synthesis of dihydropyrimidinones: improved conditions for the Biginelli reaction,” Synlett, no. 1, pp. 63–64, 2000. View at Google Scholar · View at Scopus
  26. G. Sabitha, G. S. K. Reddy, C. S. Reddy, and J. S. Yadav, “One-pot synthesis of dihydropyrimidinones using iodotrimethylsilane. Facile and new improved protocol for the Biginelli reaction at room temperature,” Synlett, no. 6, pp. 858–860, 2003. View at Google Scholar · View at Scopus
  27. A. V. Narsaiah, A. K. Basak, and K. Nagaiah, “Cadmium chloride: an efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Synthesis, no. 8, pp. 1253–1256, 2004. View at Google Scholar · View at Scopus
  28. V. N. Pathak, R. Gupta, and B. Varshney, “An efficient, inexpensive “Green Chemistry” route to multicomponent Biginelli condensation catalyzed by CuCl2.2H2O-HCl,” Indian Journal of Chemistry B, vol. 47, no. 3, pp. 434–438, 2008. View at Google Scholar · View at Scopus
  29. A. A. Ashraf and Abdel-Fattah, “Expedient synthesis of Biginelli-type dihydropyrimidinones using α-(benzotriazolyl)alkyl urea derivatives,” Synthesis, no. 15, pp. 2358–2362, 2003. View at Google Scholar · View at Scopus
  30. S. H. Chandak, P. N. Lad, and P. P. Upare, “Recyclable amberlyst-70 as a catalyst for Biginelli reaction: an efficient one-pot green protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones,” Catalysis Letters, vol. 131, no. 3-4, pp. 469–473, 2009. View at Publisher · View at Google Scholar · View at Scopus
  31. K.-Y. Lee and K.-Y. Ko, “Envirocat EPZ-10: a recyclable solid acid catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones,” Bulletin of the Korean Chemical Society, vol. 25, no. 12, pp. 1929–1931, 2004. View at Google Scholar · View at Scopus
  32. A. Chaskar, F. Jaffer, B. Langi, S. Yewale, and A. Bodkhe, “Indion 190 resin: a green and recyclable catalyst for facile and efficient one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-one,” Journal of the Korean Chemical Society, vol. 53, no. 2, pp. 224–228, 2009. 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 · View at Scopus
  34. Z.-T. Wang, L.-W. Xu, C.-G. Xia, and H.-Q. Wang, “Novel Biginelli-like three-component cyclocondensation reaction: efficient synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones,” Tetrahedron Letters, vol. 45, no. 42, pp. 7951–7953, 2004. View at Google Scholar · View at Scopus
  35. A. Saini, S. Kumar, and J. S. Sandhu, “Aluminium(III) halides mediated synthesis of 5-unsustituted 3,4-dihydropyrimidin-2(1H)-ones via three component Biginelli-like reaction,” Indian Journal of Chemistry B, vol. 46, no. 10, pp. 1690–1694, 2007. View at Google Scholar · View at Scopus