Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New and Convenient Method for Reduction of Oximes to Amines with NaBH3CN In the Presence of MoCl5/NaHSO4·H2O System

  • Kouhkan, Mehri (Department of Chemistry, Faculty of Science, Urmia University) ;
  • Zeynizadeh, Behzad (Department of Chemistry, Faculty of Science, Urmia University)
  • Received : 2011.05.16
  • Accepted : 2011.07.21
  • Published : 2011.09.20
Download PDF
⟨ Previous Next ⟩

Abstract

Various aldoximes and ketoximes were efficiently reduced to their corresponding amines with $NaBH_3CN$ in the presence of $MoCl_5/NaHSO_4{\cdot}H_2O$ system. Reduction reactions were carried out in refluxing EtOH or DMF within 0.3-3.8 h to afford the amines in high to excellent yields.

Keywords

References

  1. Hudlicky, M. Reductions in Organic Chemistry; Ellis Horwood: Chichester, 1984.
  2. Abdel-Magid, A. F. Reductions in Organic Synthesis; ACS Symposium Series, 1996; Vol. 641.
  3. Burke, S. D.; Danheiser, R. L. Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents; Wiley-VCH: New York, 1999.
  4. Andersson, P. G.; Munslow, I. J. Modern Reduction Methods; Wiley-VCH: New York, 2008.
  5. Seyden-Penne, J. Reductions by the Alumino and Borohydrides in Organic Synthesis, 2nd ed.; Wiley-VCH: New York, 1997.
  6. Review: Firouzabadi, H.; Zeynizadeh. B. Iranian J. Sci. Tech. Trans. A 1995, 19, 103.
  7. Firouzabadi, H.; Zeynizadeh, B. Bull. Chem. Soc. Jpn. 1997, 70, 155. https://doi.org/10.1246/bcsj.70.155
  8. Firouzabadi, H.; Adibi, M.; Zeynizadeh, B. Synth. Commun. 1998, 28, 1257. https://doi.org/10.1080/00397919808005968
  9. Zeynizadeh, B. Bull. Chem. Soc. Jpn. 2003, 76, 317. https://doi.org/10.1246/bcsj.76.317
  10. Zeynizadeh, B.; Shirini, F. Bull. Korean Chem. Soc. 2003, 24, 295. https://doi.org/10.5012/bkcs.2003.24.3.295
  11. Zeynizadeh, B.; Faraji, F. Bull. Korean Chem. Soc. 2003, 24, 453. https://doi.org/10.5012/bkcs.2003.24.4.453
  12. Zeynizadeh, B.; Yahyaei, S. Bull. Korean Chem. Soc. 2003, 24, 1664. https://doi.org/10.5012/bkcs.2003.24.11.1664
  13. Zeynizadeh, B.; Shirini, F. J. Chem. Res. 2003, 335.
  14. Zeynizadeh, B.; Zahmatkesh, K. J. Chem. Res. 2003, 522.
  15. Zeynizadeh, B.; Zahmatkesh, K. J. Chin. Chem. Soc. 2003, 50, 267.
  16. Zeynizadeh, B. Z. Naturforsch. 2003, 58b, 1220.
  17. Zeynizadeh, B.; Yahyaei, S. Z. Naturforsch. 2004, 59b, 699.
  18. Zeynizadeh, B.; Yahyaei, S. Z. Naturforsch. 2004, 59b, 704.
  19. Zeynizadeh, B.; Behyar, T. Bull. Chem. Soc. Jpn. 2005, 78, 307. https://doi.org/10.1246/bcsj.78.307
  20. Zeynizadeh, B.; Behyar, T. J. Braz. Chem. Soc. 2005, 16, 1200. https://doi.org/10.1590/S0103-50532005000700018
  21. Zeynizadeh, B.; Zahmatkesh, K. J. Chin. Chem. Soc. 2005, 52, 109.
  22. Zeynizadeh, B. J. Chin. Chem. Soc. 2005, 52, 525.
  23. Zeynizadeh, B.; Setamdideh, D. J. Chin. Chem. Soc. 2005, 52, 1179.
  24. Zeynizadeh, B.; Behyar, T. Z. Naturforsch. 2005, 60b, 453.
  25. Zeynizadeh, B.; Ghasemi, H. J. Chem. Res. 2006, 542.
  26. Zeynizadeh, B.; Setamdideh, D. Synth. Commun. 2006, 36, 2699. https://doi.org/10.1080/00397910600764709
  27. Setamdideh, D.; Zeynizadeh, B. Z. Naturforsch. 2006, 61b, 1275.
  28. Zeynizadeh, B.; Setamdideh, D., Faraji, F. Bull. Korean Chem. Soc. 2008, 29, 76. https://doi.org/10.5012/bkcs.2008.29.1.076
  29. Zeynizadeh, B.; Setamdideh, D. Asian J. Chem. 2009, 21, 3603.
  30. Hutchins, R. O.; Maryanoff, B. E.; Milewski, C. A. J. Am. Chem. Soc. 1971, 93, 1793. https://doi.org/10.1021/ja00736a044
  31. Hutchins, R. O.; Milewski, C. A.; Maryanoff, B. E. J. Am. Chem. Soc. 1973, 95, 3662. https://doi.org/10.1021/ja00792a033
  32. Hutchins, R. O.; Kacher, M.; Rua, L. J. Org. Chem. 1975, 40, 923. https://doi.org/10.1021/jo00895a024
  33. Lane, C. F. Synthesis 1975, 135.
  34. Hutchins, R. O.; Rotstein, D.; Natale, N.; Fanelli, J. J. Org. Chem. 1976, 41, 3328. https://doi.org/10.1021/jo00882a029
  35. Hutchins, R. O.; Kandasamy, D.; Maryanoff, C. A.; Masilamani, D.; Maryanoff, B. E. J. Org. Chem. 1977, 42, 82. https://doi.org/10.1021/jo00421a016
  36. Hutchins, R. O.; Taffer, I. M.; Burgoyne, W. J. Org. Chem. 1981, 46, 5214. https://doi.org/10.1021/jo00338a031
  37. Kim, S.; Oh, C. H.; KO, J. S.; Ahn, K. H.; Kim, Y. J. J. Org. Chem. 1985, 50, 1927. https://doi.org/10.1021/jo00211a028
  38. Han, O.; Shih, Y.; Liu, L.-D.; Liu, H.- W. J. Org. Chem. 1988, 53, 2105. https://doi.org/10.1021/jo00244a050
  39. Paquette, L. A.; Crich, D.; Fuchs, P. L.; Molander, G. A. Encyclopedia of Reagents for Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2009.
  40. Ricci, A. Modern Amination Methods; Wiley-VCH: Weinheim, 2000.
  41. Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: U.K. 2004.
  42. Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications; Wiley-VCH: Weinheim, 2010.
  43. Farooqui; T.; Farooqui, A. A. Biogenic Amines: Pharmacological, Neurochemical and Molecular Aspects in the CNS; Nova Science Publisher: New York, 2010.
  44. Hagen, J. Industrial Catalysis: a Practical Approach, 2nd ed.; Wiley-VCH: Weinheim, 2006.
  45. b) Arpe, H. -J. Industrial Organic Chemistry, 5th ed.; Wiley-VCH: Weinheim, 2010.
  46. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897. https://doi.org/10.1021/ja00741a013
  47. Leeds, J. P.; Kirst, H. A. Synth. Commun. 1988, 18, 777. https://doi.org/10.1080/00397918808057845
  48. Kouhkan, M.; Zeynizadeh, B. Bull. Korean Chem. Soc. 2010, 31, 2961. https://doi.org/10.5012/bkcs.2010.31.10.2961
  49. Zeynizadeh, B.; Amjadi, E. Asian J. Chem. 2009, 21, 3611 and the references cited therein.

Cited by

  1. O System. vol.43, pp.9, 2012, https://doi.org/10.1002/chin.201209036
  2. The efficient solvent-free reduction of oximes to amines with NaBH3CN catalyzed by ZrCl4/nano Fe3O4 system vol.12, pp.5, 2015, https://doi.org/10.1007/s13738-014-0550-3
  3. Rapid and green reduction of aromatic/aliphatic nitro compounds to amines with NaBH4 and additive Ni2B in H2O vol.12, pp.7, 2015, https://doi.org/10.1007/s13738-014-0585-5
  4. Detailed studies on the reduction of aliphatic 3-, 4-, 6-, and 13-oximino esters: Synthesis of novel isomeric amino esters, oximino alcohols, and amino alcohols vol.47, pp.22, 2017, https://doi.org/10.1080/00397911.2017.1364768
  5. Study of the Lyase Activity of Human DNA Polymerase β Using Analogues of the Intermediate Schiff Base Complex vol.57, pp.18, 2011, https://doi.org/10.1021/acs.biochem.8b00308
  6. Heterogeneous palladium-based catalyst promoted reduction of oximes to amines: using H2 at 1 atm in H2O under mild conditions vol.4, pp.6, 2011, https://doi.org/10.1039/c9re00003h
  7. Green, rapid, and highly efficient syntheses of α , α′ ‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones as potentially bi vol.67, pp.4, 2011, https://doi.org/10.1002/jccs.201900081
  8. Semi‐Synthetic Sialic Acid Probes for Challenging the Substrate Promiscuity of Enzymes in the Sialoconjugation Pathway vol.362, pp.23, 2011, https://doi.org/10.1002/adsc.202000859