Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Simple, Efficient, Catalyst-Free and Solvent-Less Microwave-Assisted Process for N-Cbz Protection of Several Amines

  • Aouf, Zineb (Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Department of Chemistry, Sciences Faculty, - Badji Mokhtar - Annaba University) ;
  • Mansouri, Rachida (Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Department of Chemistry, Sciences Faculty, - Badji Mokhtar - Annaba University) ;
  • Lakrout, Salah (Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Department of Chemistry, Sciences Faculty, - Badji Mokhtar - Annaba University) ;
  • Berredjem, Malika (Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Department of Chemistry, Sciences Faculty, - Badji Mokhtar - Annaba University) ;
  • Aouf, Nour-Eddine (Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Department of Chemistry, Sciences Faculty, - Badji Mokhtar - Annaba University)
  • Received : 2017.03.28
  • Accepted : 2017.06.15
  • Published : 2017.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, ${\beta}$-amino alcohols, ${\alpha}$-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxycarbamates compounds were obtained in short times without any side products.

Keywords

References

  1. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed, Wiley: New York, 2007.
  2. Kocienski, P. J. Protecting Groups, 3rd ed, George Thieme Verlage: New York, 2004.
  3. Kim, T. H.; Chun, J. C. Bull. Kor. Chem. Soc. 2003, 24, 157. https://doi.org/10.5012/bkcs.2003.24.2.157
  4. Sajiki, H. Tetrahedron Lett. 1995, 36, 3465. https://doi.org/10.1016/0040-4039(95)00527-J
  5. Kumar, V. P.; Reddy, M. S.; Narender, M.; Surendra, K.; Nageswar, Y. V. D.; Rama Rao, K. Tetrahedron Lett. 2006, 47, 6393. https://doi.org/10.1016/j.tetlet.2006.06.162
  6. Hernandez, J. N.; Martin, V. S. J. Org. Chem. 2004, 69, 3590. https://doi.org/10.1021/jo049759+
  7. Babu, K. S.; Rao, V. R. S.; Rao, R. R.; Babu, S. S.; Reo, J. M. Can. J. Chem. 2009, 87, 393. https://doi.org/10.1139/v08-169
  8. Gawante, M. B.; Polshettiwar, V. R.; Varma, S.; Jawaram, R. V. Tetrahedron Lett. 2006, 48, 8170.
  9. Mahesh, K. C.; Narasimhulu, M.; Reddy, T. S.; Venkateswarlu, N. S. A. Tetrahedron Lett. 2007, 48, 55. https://doi.org/10.1016/j.tetlet.2006.11.015
  10. Varala, R.; Enugala, R.; Adapa, S. R. J. Iran. Chem. Soc. 2007, 4, 370. https://doi.org/10.1007/BF03245988
  11. Suryakiran, N.; Mahesh, K. C.; Ramesh, D.; Paul, S. J. J.; Venkateswarlu, Y. Tetrahedron Lett. 2008, 49, 2607. https://doi.org/10.1016/j.tetlet.2008.02.108
  12. Shkhande, J.; Gawande, M. B.; Jayaram, R. V. Tetrahedron Lett. 2008, 49, 4799. https://doi.org/10.1016/j.tetlet.2008.05.010
  13. Zhang, C. L.; Zhang, D. F.; Zhao, H. Y.; Lin, Z. Y.; Huang Chin, H. H. Chem. Lett. 2012, 23, 789.
  14. Yadav, V. K.; Babu, K. G. J. Org. Chem. 2004, 69, 577. https://doi.org/10.1021/jo035412f
  15. Bora, P. P.; Vanlaldinpuia, K.; Rokhum, L.; Bez, G. Synth. Commu. 2011, 41, 2674. https://doi.org/10.1080/00397911.2010.515341
  16. Larhed, M.; Olofsson, K. Micowave Methods in Organic Synthesis, Sringger-Verlag: Berlin, Heidelderg, 2006.
  17. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279. https://doi.org/10.1016/S0040-4039(00)83996-9
  18. Guiguere, R. J.; Bray, T. L.; Duncun, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4954.
  19. K'tir, H.; Amira, A.; Berredjem, M.; Aouf, N.-E. Chem. Lett. 2014, 43, 851. https://doi.org/10.1246/cl.140075
  20. Lakrout, S.; K'tir, H.; Amira, A.; Berredjem, M.; Aouf, N.-E., RSC. Adv. 2014, 4, 16027. https://doi.org/10.1039/C4RA01346H
  21. Ouarna, S.; K'tir, H.; Lakrout, S.; Ghorab, H.; Aouf, Z.; Berredjem, M.; Aouf, N.-E., J. Orient. Chem. 2015, 31, 2.
  22. Mansouri, R.; Aouf, Z.; Lakrout, S.; Berredjem, M.; Aouf, N-E. J. Braz. Chem. Soc. 2016, 3, 546.
  23. Amira, A. Ph. D. Thesis, Synthese, Reactivite et Evaluation de l'Activite Biologique d'Heterocycles Azotes : Conception de Nouveaux Agents Alkylants & Protection N-Boc d'Amines Assistee par Ultrasons, Badji Mokhtar-Annaba University, 2015.
  24. Amira, A.; K'tir, H.; Becheker, I.; Ouarna, S.; Inguimbert, N.; Berredjem, H.; Berredjem, M.; Aouf, N.-E. Der. Pharma. Chemica. 2015, 7, 213.
  25. Hock, S.; Martib, R.; Riedla, R.; Simeunovicc, M. CHIMIA, 2010, 64, 200. https://doi.org/10.2533/chimia.2010.200