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http://dx.doi.org/10.5012/bkcs.2010.31.7.1927

One-Pot Reductive Amination of Carbonyl Compounds Using Sodium Borohydride-Cellulose Sulfuric Acid  

Alinezhad, Heshmatollah (Faculty of Chemistry, Mazandaran University)
Tollabian, Zakieh (Faculty of Chemistry, Mazandaran University)
Publication Information
Abstract
A fast, efficient, and high yielding method for the preparation of amines by reductive amination of aldehydes and ketones using sodium borohydride in the presence of cellulose sulfuric acid in EtOH and under solvent-free conditions at room temperature is described.
Keywords
Cellulose sulfuric acid; Reductive amination; Carbonyl compounds; Amines; $NaBH_4$;
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1 Bhanushali, M. J.; Nandurkar, N. S.; Bhor, M. D.; Bhanage B. M. Tetrahedron Lett. 2007, 48, 1273.   DOI
2 Alinezhad, H.; Tajbakhsh, M.; Mahdavi, N. Syn. Commun. 2010, 40, 951.   DOI
3 Alinezhad, H.; Tajbakhsh, M.; Hamidi, N. Turk. J. Chem. 2010, 34, 1.
4 Alinezhad, H.; Tajbakhsh, M.; Hamidi, N. Chin. Chem. Lett. 2010, 21, 7.   DOI
5 Rylabder, P. N. Hydrogenation Methods; Academic Press: New York, 1985.
6 Ryschkewitsch, G. E.; Birnbaum, E. R. Inorg. Chem. 1965, 4, 575.   DOI
7 Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549.   DOI
8 Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.   DOI
9 Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 6.
10 Shaabani, A.; Maleki, A. Appl. Catal. A 2007, 331, 149.   DOI
11 Kim, S.; Oh, C. H.; Ko, J. S.; Ahn, K. H.; Kim, Y. J. Org. Chem. 1985, 50, 1927.   DOI
12 Onaka, M.; Umezono, A.; Kawai, M.; Izumi, Y. J. Chem. Soc. Chem. Commun. 1985, 17, 1202.
13 Alinezhad, H.; Tajbakhsh, M.; Salehian, F.; Fazli, K. Tetrahedron Lett. 2009, 50, 659.   DOI
14 Alinezhad, H.; Tajbakhsh, M.; Zare, M. Syn. Commun. 2009, 39, 2907.   DOI
15 Watanabe, Y.; Tsuji, Y.; Ige, H.; Ohsugi, Y.; Ohta, T. J. Org. Chem. 1984, 49, 3359.   DOI
16 Kessar, S. V.; Gopal, R.; Singh, M. Tetrahedron 1973, 29, 167.   DOI
17 Cho, B. T.; Kang, S. K. Synlett 2004, 1484.
18 Vijayaraj, M.; Gopinath, C. H. Appl. Catal. 2007, 320, 807.
19 Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.   DOI
20 Ranu, B. C.; Majee, A.; Sarkar, A. J. Org. Chem. 1998, 63, 370.   DOI
21 Neidigh, K. A.; Avery, M. A.; Williamson, J. C.; Bhattacharyya, S. J. Chem. Soc. Perkin Trans. 1 1998, 2527.
22 Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 10, 1079.
23 Verardo, G.; Giumanin, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121.
24 Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928.   DOI
25 Saxena, I.; Borah, R.; Sarma, J. C. J. Chem. Soc. Perkin Trans. 1 2000, 503.
26 Varma, R. S.; Dahiya, R. Tetrahedron 1998, 54, 6293.   DOI
27 Bomann, M. D.; Guch, I. C.; Dimare, M. J. Org. Chem. 1995, 60, 5995.   DOI
28 Cho, B. T.; Kang, S. K. Tetrahedron 2005, 61, 5725.   DOI
29 Firouzabadi, H.; Iranpoor, N.; Alinezhad, H. Bull. Chem. Soc. Jpn. 2003, 76, 143.   DOI
30 Chen, B. C.; Sundeen, J. E.; Guo, P.; Bednarz, M. S.; Zhao, R. Tetrahedron Lett. 2001, 42, 1245.   DOI
31 Alinezhad, H.; Tajbakhsh, M.; Salehian, F. Monatsh. Chem. 2005, 136, 2029.   DOI
32 Alinezhad, H.; Tajbakhsh, M.; Zamani, R. Synlett 2006, 431.
33 Alinezhad, H.; Ardestani, E. Lett. Org. Chem. 2007, 4, 473.   DOI
34 Alinezhad, H.; Tajbakhsh, M.; Enayati Ahangar, R. Monatsh. Chem. 2008, 13, 21.
35 Nugent, T. C.; Ghosh, A. K.; Wakchaure, V. N.; Mohanty, R. R. Adv. Synth. Catal. 2006, 348, 1289.   DOI
36 Hutchins, R. O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 25.
37 Gustafsson, M.; Olsson, R.; Anderson, C. M. Tetrahedron Lett. 2001, 42, 133.   DOI
38 Tarasevich, V. A.; Kozlov, N. G. Russ. Chem. Rev. 1999, 68, 55.   DOI
39 Lane, C. F. Synthesis 1975, 135.
40 Abdel-Magid, A. F.; Maryanoff, C. F.; Carson, K. C. Tetrahedron Lett. 1990, 31, 5595.   DOI
41 Mohanazadeh, F.; Forozani, M.; Taheri, A. Monatsh. Chem. 2007, 138, 1187.   DOI
42 Abdel-Magid, A. F.; Maryanoff, C. F. Synlett 1990, 537.