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http://dx.doi.org/10.5012/jkcs.2017.61.4.151

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)
Publication Information
Journal of the Korean Chemical Society / v.61, no.4, 2017 , pp. 151-156 More about this Journal
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
Amine; Benzyl chloroformate (Cbz-Cl); Protection; Microwave-assisted; Solvent-free;
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  • Reference
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.   DOI
4 Sajiki, H. Tetrahedron Lett. 1995, 36, 3465.   DOI
5 Kumar, V. P.; Reddy, M. S.; Narender, M.; Surendra, K.; Nageswar, Y. V. D.; Rama Rao, K. Tetrahedron Lett. 2006, 47, 6393.   DOI
6 Hernandez, J. N.; Martin, V. S. J. Org. Chem. 2004, 69, 3590.   DOI
7 Babu, K. S.; Rao, V. R. S.; Rao, R. R.; Babu, S. S.; Reo, J. M. Can. J. Chem. 2009, 87, 393.   DOI
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.   DOI
10 Varala, R.; Enugala, R.; Adapa, S. R. J. Iran. Chem. Soc. 2007, 4, 370.   DOI
11 Suryakiran, N.; Mahesh, K. C.; Ramesh, D.; Paul, S. J. J.; Venkateswarlu, Y. Tetrahedron Lett. 2008, 49, 2607.   DOI
12 Shkhande, J.; Gawande, M. B.; Jayaram, R. V. Tetrahedron Lett. 2008, 49, 4799.   DOI
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.   DOI
15 Lakrout, S.; K'tir, H.; Amira, A.; Berredjem, M.; Aouf, N.-E., RSC. Adv. 2014, 4, 16027.   DOI
16 Bora, P. P.; Vanlaldinpuia, K.; Rokhum, L.; Bez, G. Synth. Commu. 2011, 41, 2674.   DOI
17 Larhed, M.; Olofsson, K. Micowave Methods in Organic Synthesis, Sringger-Verlag: Berlin, Heidelderg, 2006.
18 Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279.   DOI
19 Guiguere, R. J.; Bray, T. L.; Duncun, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4954.
20 K'tir, H.; Amira, A.; Berredjem, M.; Aouf, N.-E. Chem. Lett. 2014, 43, 851.   DOI
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.   DOI