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http://dx.doi.org/10.5012/jkcs.2007.51.4.361

One-Pot Efficient Beckmann Rearrangement of Ketones Catalyzed by Silica Sulfuric Acid  

Eshghi, H. (Department of Chemistry, Ferdowsi University of Mashhad)
Hassankhani, A. (Department of Chemistry, Sistan & Baluchestan University)
Publication Information
Abstract
A one-pot Beckmann rearrangement for the preparation of amides from ketones is described using the silica sulfuric acid under Microwave irradiation. Advantages of this method are regioselectivity with high yields in a simple operation and short reaction time, in which the mole ratio of acid and ketone was 1:2 and it should be greener than the currently used systems.
Keywords
SilIca Sulfuric Acid; Ketones; Amides; Microwave Irradiation; Beckmann Rearrangement;
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1 Beckmann, E. Chem. Ber. 1886, 19, 988   DOI
2 Izumi, Y.; Sato, S.; Urabe, K. Chem. Lett. 1983, 1649
3 Luca, L. D.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272   DOI   ScienceOn
4 Yadav, J. S.; Reddy, B. V. S.; Madhavi, A. V.; Ganesh, Y. S. S. J. Chem. Res. (S) 2002, 236
5 Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311   DOI   ScienceOn
6 Kikugawa, Y.; Tsuji, C.; Miyazawa, E.; Sakamoto, T. Tetrahedron Lett. 2001, 42, 2337   DOI   ScienceOn
7 Anilkumar, R.; Chandrasekhar, S. Tetrahedron Lett. 2000, 41, 5427   DOI   ScienceOn
8 Thakur, A. J.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synth. Commun. 2000, 30, 2105   DOI   ScienceOn
9 Sato, H.; Yoshioka, H.; Izumi, Y. J. Mol. Catal. A: Chemical, 1999, 149, 25
10 Bhawal, B. M.; Mahabhate, S. P.; Likhite, A. P.; Deshmukh, A. R. A. S. Synth. Commun. 1995, 25, 3315   DOI   ScienceOn
11 Ko, Y.; Kim, M. H.; Kim, S. J.; Seo, G.; Kim, M. Y.; Uh, Y. S. Chem. Commun. 2000, 829
12 Dai, L. X.; Koyama, K.; Miyamoto, M.; Tatsumi, T. Appl. Catal. A: Gen. 1999, 189, 237   DOI   ScienceOn
13 Ushikubo, T.; Wada, K. J. Catal. 1994, 148, 138   DOI   ScienceOn
14 Izumi, Y. Chem. Lett. 1990, 2171
15 Khodaei, M. M.; Meybodi, F. A.; Rezai, N.; Salehi, P. Synth. Commun. 2001, 31, 941
16 Ghiaci, M.; Imanzadeh, H. Synth. Commun. 1998, 28, 2275   DOI   ScienceOn
17 Ganboa, I.; Palomo, C. Synth. Commun. 1983, 13, 941   DOI   ScienceOn
18 Sharghi, H.; Hosseini, M. Synthesis 2002, 1057
19 Sharghi, H.; Hosseini, M. J. Chem. Research (S), 2003, 176
20 Eshghi, H.; Gordi, Z. Synth. Commun. 2003, 33, 2971   DOI   ScienceOn
21 Gawly, R. E.; Org. React. 1988, 35, 1
22 Donaruma, L. G.; Heldt, W. Z. Org. React. 1960, 11, 1
23 Smith, M. B.; March, J. Advanced Organic Chemistry; John Wiely & Sons: New York, U. S. A., 2001, 5th ed., p 1415
24 Laurent, A.; Jacquault, P.; Di Martino, J. L.; Hamelin, J. J. Chem. Soc., Chem. Commun. 1995, 1101
25 Imamato, T.; Yokoyama. H.; Yokoyama, M. Tetrahedron Lett. 1981, 22, 1803   DOI   ScienceOn
26 Jung, M. E.; Zeng, L. M. Tetrahedron Lett. 1983, 24, 4533   DOI   ScienceOn
27 Kamiju, T.; Harada, H.; Lizuka, K. Chem. Pharm. Bull. 1984, 32, 2560   DOI
28 Pai, S. G.; Bajpai, A. R.; Deshpande, A. B.; Samant, S. D. Synth. Commun. 1997, 27, 379   DOI   ScienceOn
29 Bosch, A. I.; De la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa, F. Synlett, 1995, 1259
30 Meshram, H. M. Synth. Commun. 1990, 20, 3253   DOI
31 Reddy, J. S.; Ravishankar, R.; Sivasankar, S.; Ratnaswamy, P. Catal. Lett. 1993, 17, 139   DOI
32 Zolfigol, M. A. Tetrahedron 2001, 57, 9509   DOI   ScienceOn
33 Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J. Lett. Org. Chem. 2005, 2, 444   DOI   ScienceOn
34 Kira, M. A.; Shaker, Y. M. Egypt. J. Chem. 1973, 6, 551
35 Li, D.; Shi, F.; Guo, S.; Deng, Y. Tetrahedron Lett. 2005, 46, 671   DOI   ScienceOn
36 Conly, R. T. J. Org. Chem. 1958, 23, 1330   DOI
37 Olah, G. A.; Fung, A. P. Synthesis, 1979, 537
38 R. C. Weast and J. G. Grasselli, Handbook of Data on Organic Compounds; 2nd Ed.; 1989
39 A. I. Vogel, Text Book of Practical Organic Chemistry; 4th Ed.; Longman: London, U. K., 1986