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Silica Supported Fluoroboric Acid: An Efficient and Reusable Heterogeneous Catalyst for Facile Synthesis of 2-Aliphatic Benzothiazoles, Benzoxazoles, Benzimidazoles and Imidazo[4,5-b]pyridines

  • Patil, Abasaheb V. (School of Semiconductor and Chemical Engineering, Nanomaterials Processing Research Center, Chonbuk National University) ;
  • Bandgar, Babasaheb P. (Organic Chemistry Research Laboratory, School of Chemical Sciences, Swami Ramanand Teerth Marathwada University) ;
  • Lee, Soo-Hyoung (School of Semiconductor and Chemical Engineering, Nanomaterials Processing Research Center, Chonbuk National University)
  • 투고 : 2009.11.16
  • 심사 : 2010.02.22
  • 발행 : 2010.06.20

초록

키워드

참고문헌

  1. Denny, W. A.; Revacastle, G. W.; Baguley, B. J. Med. Chem. 1990, 33, 814. https://doi.org/10.1021/jm00164a054
  2. Israel, M.; Day, A. R. J. Org. Chem. 1959, 24, 1455. https://doi.org/10.1021/jo01092a018
  3. Kassidy, P. E. Thermally Stable Polymers; Marcell Dekkar: New York, 1980.
  4. Yildiz, I. O.; Yalcin, I.; Akisener, E.; Ucarturk, N. Eur. J. Med. Chem. 2004, 39, 291. https://doi.org/10.1016/j.ejmech.2003.11.014
  5. Song, X.; Vig, B. S.; Lorenzi, P. L.; Drach, J. C.; Townsend, L. B.; Amidon, G. L. J. Med. Chem. 2005, 48, 1274. https://doi.org/10.1021/jm049450i
  6. Yamato, M. J. Pharm. Soc. Jpn. 1992, 112, 81.
  7. Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Karvin, S. M. Bioorg. Med. Chem. 2002, 10, 3997. https://doi.org/10.1016/S0968-0896(02)00327-9
  8. Benazzouz, A.; Boraud, T.; Dubedat, P.; Boireau, A.; Stutzmann, J. M.; Gross, C. Eur. J. Pharmacol. 1995, 284, 299. https://doi.org/10.1016/0014-2999(95)00362-O
  9. Grimmett, M. R.; Katritzky, A. R.; Rees, C. W.; Sceiven, E. F. V.; Comprehensive Heterocyclic Chemistry II, Vol 3; Elsevier Science Ltd: Oxford, 1996.
  10. Alcalde, E.; Dinares, I.; Perez-Garcia, L.; Roca, T. Synthesis 1992, 395.
  11. Pottorf, R. S.; Chadha, N. K.; Katkevics, M.; Ozola, V.; Suna, E.; Ghane, H.; Regberg, T.; Player, M. R. Tetrahedron Lett. 2003, 44, 175. https://doi.org/10.1016/S0040-4039(02)02495-4
  12. Nadaf, R. N.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Mol. Catal. A: Chem. 2004, 214, 155. https://doi.org/10.1016/j.molcata.2003.10.064
  13. Jenkins, G. L.; Knevel, A. M.; Davis, C. S. J. Org. Chem. 1961, 26, 274.
  14. Doise, M.; Dennin, F.; Blondeau, D.; Sliwa, H. Tetrahetron Lett. 1990, 31, 1155. https://doi.org/10.1016/S0040-4039(00)88750-X
  15. Villemin, D.; Hammadi, M; Martin, B. Synthetic Commun. 1996, 26, 2895. https://doi.org/10.1080/00397919608005224
  16. Chakraborti, A. K.; Rudrawar, S.; Kaur, G.; Sharma, L. Synlett 2004, 1533.
  17. Hari, A.; Karan, C.; Rodridues, W. C.; Miller, B. L. J. Org. Chem. 2001, 66, 991. https://doi.org/10.1021/jo005758f
  18. Beaulieu, P. L.; Hache, B.; Von Moss, E. Synthesis 2003, 1683.
  19. Curini, M.; Epifano, F.; Montanari, F.; Rosati, O.; Taccone, S. Synlett 2004, 1832.
  20. Gogoi, P.; Konwar, D. Tetrahedron Lett. 2006, 47, 79. https://doi.org/10.1016/j.tetlet.2005.10.134
  21. Trivedi, R.; De, S. K.; Gibbs, R. A. J. Mol. Catal. A: Chem. 2006, 245, 8. https://doi.org/10.1016/j.molcata.2005.09.025
  22. Navarrete-Vazquez, G.; Moreno-Diaz, H.; Aguirre-Crespo, F.; Leon-Revara, I.; Villalobos-Molina, R.; Munoz-Muniz, O.; Estrada-Soto, S. Bioorg. Med. Chem. Lett. 2006, 16, 4169. https://doi.org/10.1016/j.bmcl.2006.05.082
  23. Boyd, G. V.; Katritzky, A. R.; Rees, C. W.; Potts, K. T. Comprehensive Heterocyclic Chemistry; Pregamon Press: New York, 1984; p 177.
  24. Bu, X. Z.; Huang, Z. S.; Zhang, M.; Ma, L.; Xiao, G. W.; Gu, L. Q. Tetrahedron Lett. 2001, 42, 5737. https://doi.org/10.1016/S0040-4039(01)01034-6
  25. Bhaval, B. M.; Mayabhate, S. P.; Likhite, A. P.; Deshmukh, A. R. A. S. Synthetic Commun. 1995, 25, 3315. https://doi.org/10.1080/00397919508013850
  26. Tundo, D.; Anastas, P. T.; Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
  27. Toda, F. Acc. Chem. Res. 1995, 28, 480. https://doi.org/10.1021/ar00060a003
  28. Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896.
  29. Hajipoor, A. R.; Abidi, H.; Rooho, A. E. J. Org. Chem. 2003, 68, 4553. https://doi.org/10.1021/jo034217y
  30. Bandgar, B. P.; Patil, A. V.; Kamble, V. T. Arkivoc 2007, 16, 252.
  31. Bandgar, B. P.; Patil, A. V.; Kamble, V. T.; Totre, J. V. J. Mol. Catal. A: Chem. 2007, 273, 114. https://doi.org/10.1016/j.molcata.2007.02.051
  32. Bandgar, B. P.; Patil, A. V.; Kamble, V. T.; Chavan, O. S. Cat. Commun. 2007, 8, 1065. https://doi.org/10.1016/j.catcom.2006.10.003
  33. Bandgar, B. P.; Patil, A. V.; Chavan, O. S. J. Mol. Catal. A: Chem. 2006, 256, 99. https://doi.org/10.1016/j.molcata.2006.04.024
  34. Raban, M.; Chang, H.; Craine, L.; Hortelano, E. J. Org. Chem. 1985, 50, 2205. https://doi.org/10.1021/jo00213a001
  35. Wang, H.; Partch, R. E.; Li, Y. J. Org. Chem. 1997, 62, 5222. https://doi.org/10.1021/jo970253j
  36. Wang, L.; Sheng, J.; Tian, H.; Qian, C. Synthetic Commun. 2004, 34, 4265. https://doi.org/10.1081/SCC-200039340
  37. Joshi, A. A.; Vishwanathan, C. L. Bioorg. Med. Chem. Lett. 2006, 16, 2613. https://doi.org/10.1016/j.bmcl.2006.02.038
  38. Kumar, D.; David, W. M.; Kervin, S. M. Bioorg. Med. Chem. Lett. 2001, 11, 2971. https://doi.org/10.1016/S0960-894X(01)00606-0
  39. Heravi, M. M.; Montazeri, N.; Rahmizadeh, M.; Bakavoli, M.; Ghassemzadeh, M. J. Chem. Res. (S) 2000, 584.

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