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A Rapid and Practical Protocol for Solvent-Free Reduction of Oximes to Amines with NaBH4/ZrCl4/Al2O3 System

  • Zeynizadeh, Behzad (Department of Chemistry, Faculty of Science, Urmia University) ;
  • Kouhkan, Mehri (Department of Chemistry, Faculty of Science, Urmia University)
  • 투고 : 2011.06.13
  • 심사 : 2011.08.01
  • 발행 : 2011.09.20

초록

Solvent-free reduction of various aldoximes and ketoximes to the corresponding amines was performed easily and efficiently with $NaBH_4$ in the presence of $ZrCl_4$ supported on $Al_2O_3$. The reactions were carried out rapidly (within 2 min) at room temperature to afford the amines in high to excellent yields.

키워드

참고문헌

  1. Andersson, P. G.; Munslow, I. J. Modern Reduction Methods; Wiley-VCH: New York, 2008.
  2. Burke, S. D.; Danheiser, R. L. Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents; Wiley-VCH: New York, 1999.
  3. Seyden- Penne, J. Reductions by the Alumino and Borohydrides in Organic Synthesis; 2nd ed., Wiley-VCH: New York, 1997.
  4. Abdel- Magid, A. F. Reductions in Organic Synthesis; ACS Symposium Seies, 1996. Vol. 641.
  5. Hudlicky, M. Reductions in Organic Chemistry; Ellis Horwood: Chichester, 1984.
  6. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849. https://doi.org/10.1021/jo960057x
  7. Nutaitis, C. F.; Bernardo, J. E. J. Org. Chem. 1989, 54, 5629. https://doi.org/10.1021/jo00284a046
  8. Narayana, C.; Periasamy, M. Tetrahedron Lett. 1985, 26, 1757. https://doi.org/10.1016/S0040-4039(00)98331-X
  9. Hutchins, R. O.; Learn, K.; El-Telbany, F.; Stercho, Y. P. J. Org. Chem. 1984, 49, 2438. https://doi.org/10.1021/jo00187a028
  10. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1. https://doi.org/10.1021/jo01289a001
  11. Lane, C. F. Synthesis 1975, 135.
  12. Lalancette, J. M.; Freche, A.; Brindle, J. R.; Laliberte, M. Synthesis 1972, 526.
  13. Narasimhan, S.; Balakumar, R. Synth. Commun. 2000, 30, 4387. https://doi.org/10.1080/00397910008087061
  14. Narasimhan, S.; Balakumar, R. Aldrichimica Acta 1998, 31, 19.
  15. Ravi Kumar, K. S.; Baskaran, S.; Chandrasekaran, S. Tetrahedron Lett. 1993, 34, 171. https://doi.org/10.1016/S0040-4039(00)60086-2
  16. Fujii, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1991, 20, 1847.
  17. Soai, K.; Ookawa, A. J. Org. Chem. 1986, 51, 4000. https://doi.org/10.1021/jo00371a017
  18. Marks, T. J.; Kolb, J. R. Chem. Rev. 1977, 77, 263. https://doi.org/10.1021/cr60306a004
  19. Firouzabadi, H.; Adibi, M.; Zeynizadeh, B. Synth. Commun. 1998, 28, 1257. https://doi.org/10.1080/00397919808005968
  20. Firouzabadi, H.; Adibi, M. Phosphorus, Sulfur, Silicon Relat. Elem. 1998, 142, 125. https://doi.org/10.1080/10426509808029672
  21. Firouzabadi, H.; Adibi, M. Synth. Commun. 1996, 26, 2429. https://doi.org/10.1080/00397919608004555
  22. Firouzabadi, H.; Afsharifar, G. R. Bull. Chem. Soc. Jpn. 1995, 68, 2595. https://doi.org/10.1246/bcsj.68.2595
  23. Pasumansky, L.; Goralski, C. T.; Singaram, B. Org. Proc. Res. Dev. 2006, 10, 959. https://doi.org/10.1021/op0600759
  24. Cainelli, G.; Giacomini, D.; Panunzioa, M.; Martelli, G.; Spunta, G. Tetrahedron 1985, 41, 1385. https://doi.org/10.1016/S0040-4020(01)96540-8
  25. Blough, B. E.; Carroll, F. I. Tetrahedron Lett. 1993, 34, 7239. https://doi.org/10.1016/S0040-4039(00)79297-5
  26. Zeynizadeh, B.; Setamdideh, D. Asian J. Chem. 2009, 21, 3603.
  27. Zeynizadeh, B.; Setamdideh, D.; Faraji, F. Bull. Korean Chem. Soc. 2008, 29, 76. https://doi.org/10.5012/bkcs.2008.29.1.076
  28. Zeynizadeh, B. Bull. Chem. Soc. Jpn. 2003, 76, 317. https://doi.org/10.1246/bcsj.76.317
  29. Zeynizadeh, B.; Faraji, F. Bull. Korean Chem. Soc. 2003, 24, 453. https://doi.org/10.5012/bkcs.2003.24.4.453
  30. Zeynizadeh, B.; Zahmatkesh, K. J. Chin. Chem. Soc. 2004, 51, 801.
  31. Fleet, G. W. J.; Harding, P. J. C. Tetrahedron Lett. 1981, 22, 675. https://doi.org/10.1016/S0040-4039(01)92520-1
  32. Zeynizadeh, B.; Setamdideh, D. Asian J. Chem. 2009, 21, 3588.
  33. Haghgooie, H.; Zeynizadeh, B.; Shafaghi, M. Asian J. Chem. 2008, 20, 6033.
  34. Zeynizadeh, B.; Behyar, T. J. Braz. Chem. Soc. 2005, 16, 1200. https://doi.org/10.1590/S0103-50532005000700018
  35. Zeynizadeh, B.; Behyar, T. Bull. Chem. Soc. Jpn. 2005, 78, 307. https://doi.org/10.1246/bcsj.78.307
  36. Zeynizadeh, B.; Yahyaei, S. Bull. Korean Chem. Soc. 2003, 24, 1664. https://doi.org/10.5012/bkcs.2003.24.11.1664
  37. Zeynizadeh, B.; Shirini, F. Bull. Korean Chem. Soc. 2003, 24, 295. https://doi.org/10.5012/bkcs.2003.24.3.295
  38. Zeynizadeh, B.; Shirini, F. J. Chem. Res. 2003, 335.
  39. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763. https://doi.org/10.1021/cr00075a003
  40. Lakouraj, M. M.; Tajbakhsh, M.; Mahalli, M. S. Monatsh. Chem. 2008, 139, 117. https://doi.org/10.1007/s00706-007-0756-5
  41. Tamami, B.; Lakoraj, M. M.; Yeganeh, H. Iranian Poly. J. 1997, 6, 159.
  42. Liu, W.-Y.; Xu, Q.-H.; Ma, Y.- X. Org. Prep. Proced. Int. 2000, 32, 596. https://doi.org/10.1080/00304940009355960
  43. Sim, T. B.; Ahn, J. H.; Yoon, N. M. Synthesis 1996, 324.
  44. Yakabe, S.; Hirano, M.; Morimoto, T. Synth. Commun. 1999, 29, 295. https://doi.org/10.1080/00397919908085770
  45. Yoon, N. M.; Choi, J. Synlett 1993, 135.
  46. Firouzabadi, H.; Tamami, B.; Goudarzian, N. Synth. Commun. 1991, 21, 2275. https://doi.org/10.1080/00397919108021586
  47. Bram, G.; d'Incan, E.; Loupy, A. J. Chem. Soc. Chem. Commun. 1981, 1066.
  48. Larock, R. C. Comprehensive Organic Transformations, A Guide to Functional Group Preparations; 2nd ed., Wiley-VCH: Weinheim, 2010.
  49. Rao, H. S. P.; Bharathi, B. Indian J. Chem. 2002, 41B, 1072.
  50. Kano, S.; Tanaka, Y.; Sugino, E.; Hibino, S. Synthesis 1980, 695.
  51. Spreitzer, H.; Buchbauer, G.; Püringer, C. Tetrahedron 1989, 45, 6999. https://doi.org/10.1016/S0040-4020(01)89166-3
  52. Itsuno, S.; Sakurai, Y.; Ito, K. Synthesis 1988, 995.
  53. Bell, K. H. Aust. J. Chem. 1970, 23, 1415. https://doi.org/10.1071/CH9701415
  54. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proced. Int. 1985, 17, 317. https://doi.org/10.1080/00304948509355522
  55. Gribble, G. W.; Leiby, R. W.; Sheehan, M. N. Synthesis 1977, 856.
  56. Hutchins, R. O.; Natale, N. R. Org. Prep. Proced. Int. 1979, 11, 201. https://doi.org/10.1080/00304947909354852
  57. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897. https://doi.org/10.1021/ja00741a013
  58. Hutchins, R. O.; Learn, K.; Nazer, B.; Pytlewski, D.; Pelter, A. Org. Prep. Proced. Int. 1984, 16, 335. https://doi.org/10.1080/00304948409457891
  59. Leeds, J. P.; Kirst, H. A. Synth. Commun. 1988, 18, 777. https://doi.org/10.1080/00397918808057845
  60. Cho, B. T.; Seong, S. Y. Bull. Korean Chem. Soc. 1988, 9, 322.
  61. Bandgar, B. P.; Nikat, S. M.; Wadgaonkar, P. P. Synth. Commun. 1995, 25, 863. https://doi.org/10.1080/00397919508013422
  62. Zeynizadeh, B.; Zahmatkesh, K. J. Chin. Chem. Soc. 2005, 52, 109.
  63. Dunn, P. J.; Wells, A. S.; Williams, M. T. Green Chemistry in the Pharmaceutical Industry; Wiley-VCH: Weinheim, 2010.
  64. Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
  65. Doble, M.; Kumar, A. Green Chemistry and Engineering; Elsevier: New York, 2007.
  66. Doxsee, K.; Hutchison, J. Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments; Brooks/Cole: Belmont, CA, 2004.
  67. Tanaka, K. Solvent-free Organic Synthesis; 2nd ed., Wiley-VCH: Weinheim, 2009.
  68. Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1990, 1859.
  69. Itsuno, S.; Sakurai, Y.; Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1989, 1548.
  70. Zeynizadeh, B.; Amjadi, E. Asian J. Chem. 2009, 21, 3611

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