Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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1,3-Dichloro-5,5-dimethylhydantoin as a Novel and Efficient Homogeneous Catalyst in Biginelli Reaction

  • Received : 2010.08.10
  • Accepted : 2010.09.13
  • Published : 2010.11.20
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Abstract

A new and efficient method for the preparation of substituted 3,4-dihydropyrimidin-2(1H)-ones via Biginelli synthesis using catalytic amounts of 1,3-dichloro-5,5-dimethylhydantoin is presented. Short reaction times, easy work-up, high yields of products and stability, easy-handling, non-toxicity and cheapness of the catalyst are noteworthy advantages of the present work.

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References

  1. Aswal, K. S.; Rovnyak, G. C.; Kinball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Mallay, M. F. J. Med. Chem. 1990, 33, 2629. https://doi.org/10.1021/jm00171a044
  2. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803. https://doi.org/10.1016/S0040-4020(97)00022-7
  3. Sinder, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828. https://doi.org/10.1021/jo00067a014
  4. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. https://doi.org/10.1021/ar000048h
  5. Kappe, C. O. Tetrahedron 1993, 49, 6937. https://doi.org/10.1016/S0040-4020(01)87971-0
  6. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043. https://doi.org/10.1016/S0223-5234(00)01189-2
  7. Jain, K. S.; Bariwal, J. B.; Kathiravan, M. K.; Phoujdar, M. S.; Sahne, R. S.; Chauhan, B. S.; Shah, A. K.; Yadav, M. R. Bioorg. Med. Chem. 2008, 16, 4759. https://doi.org/10.1016/j.bmc.2008.02.091
  8. Chiang, A. N.; Valderramos, J.-C.; Balachandran, R.; Chovatiya, R. J.; Mead, B. P.; Schneider, C.; Bell, S. L.; Klein, M. G.; Huryn, D. M.; Chen, X. S.; Day, B. W.; Fidock, D. A.; Wipf, P.; Brodsky, J. L. Bioorg. Med. Chem. 2009, 17, 1527. https://doi.org/10.1016/j.bmc.2009.01.024
  9. Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; Brosse, C. D.; Mai, S.; Truneh, S.; Carte, B. J. Org. Chem. 1995, 60, 1182. https://doi.org/10.1021/jo00110a021
  10. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
  11. Chen, W.; Qin, S. D.; Jin, J. R. Catal. Commun. 2007, 8, 123. https://doi.org/10.1016/j.catcom.2006.05.026
  12. Bigdeli, M. A.; Jafari, S.; Mahdavinia, G. H.; Hazarkhani, H. Catal. Commun. 2007, 8, 1641. https://doi.org/10.1016/j.catcom.2007.01.022
  13. Khabazzadeh, H.; Saidi, K.; Sheibani, H. Bioorg. Med. Chem. Lett. 2008, 18, 278. https://doi.org/10.1016/j.bmcl.2007.10.087
  14. Rosi Reddy, K.; Venkateshwar Reddy, C. H.; Mahesh, M.; Raju, P. V. K.; Narayana Reddy, V. V. Tetrahedron Lett. 2003, 44, 8173. https://doi.org/10.1016/j.tetlet.2003.09.030
  15. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2008, 49, 6119 https://doi.org/10.1016/j.tetlet.2008.08.016
  16. Feng Yuan, N. Y. Y.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Teteahedron 2005, 58, 4801.
  17. Chitra, S.; Pandiarajan, K. Tetrahedron Lett. 2009, 50, 2222. https://doi.org/10.1016/j.tetlet.2009.02.162
  18. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465. https://doi.org/10.1016/S0040-4039(99)00424-4
  19. Legeay, J. C.; Eynde, J. J. V.; Bazureau, J. P. Tetrahedron 2008, 64, 5328. https://doi.org/10.1016/j.tet.2008.03.021
  20. Schmidt, R. J.; Lombardo, L. J.; Traeger, S. C.; Williams, D. K. Tetrahedron Lett. 2008, 49, 3009. https://doi.org/10.1016/j.tetlet.2008.02.162
  21. Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2007, 48, 7343. https://doi.org/10.1016/j.tetlet.2007.08.031
  22. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2008, 49, 6119. https://doi.org/10.1016/j.tetlet.2008.08.016
  23. Khabbazzadeh, H.; Saidi, K.; Sheibani, H. Bioorg. Med. Chem. Lett. 2008, 18, 278. https://doi.org/10.1016/j.bmcl.2007.10.087
  24. Ahmed, N.; Lier, J. E. V. Tetrahedron Lett. 2007, 48, 5407. https://doi.org/10.1016/j.tetlet.2007.06.005
  25. Cepanec, I.; Litvić, M.; Filipan Litvić, M.; Grüngold, I. Tetrahedron 2007, 63, 11822. https://doi.org/10.1016/j.tet.2007.09.045
  26. Cepanec, I.; Litvic, M.; Bartolincic, M.; Lovric, M. Tetrahedron 2005, 61, 4275. https://doi.org/10.1016/j.tet.2005.02.059
  27. Balalaie, S.; Soleiman-Beigi, M.; Rominger, F. J. Iran Chem. Soc. 2005, 2, 319. https://doi.org/10.1007/BF03245937
  28. Xu, Z.; Zhang, D.; Zou, X. Synth. Commun. 2006, 36, 255. https://doi.org/10.1080/00397910500334637
  29. Skibińska, M.; Zahn, F. A.; Czarnocka, A.; Lewenstein, W. Acta Poloniae Pharmaceutica-Drug Res. 1969, 6, 25.
  30. Khazaei, A.; Manesh, A. A. J. Chin. Chem. Soc. 2005, 52, 1017.
  31. Khazaei, A.; Manesh, A. A. Synthesis 2005, 1929.
  32. Semenova, A. A.; Korolov, A. A. Gigiena i Sanitariia 1982, 11.
  33. Neuvonen, H.; Neuvonen, K.; Koch, A.; Kleinpeter, E.; Pasanen, P. J. Org. Chem. 2002, 67, 6995. https://doi.org/10.1021/jo020121c
  34. Kappe, C. O. J. Org. Chem. 1997, 62, 7201. https://doi.org/10.1021/jo971010u

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