Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5603-5606

  Basu, Manas K ^a   Becker, Frederick F ^a   Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CHLORIDE; AROMATIC AMINE; AROMATIC NITRO COMPOUND; SAMARIUM;

ARTICLE; CATALYSIS; HYDROGENATION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; SYNTHESIS; TEMPERATURE; ULTRASOUND;

EID: 0034702560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00917-5     Document Type: Article

References (32)

1. For example, see: (a) Coleman, G. H.; Blomquist, R. F. J. Am. Chem. Soc. 1941, 63, 1692.
2. (b) Beak, P.; Kokko, B. J. Org. Chem. 1982, 47, 2822.
3. (c) Kokko, B.; Beak, P. Tetrahedron Lett. 1983, 24, 561.
4. (d) Beak, P.; Basha, A.; Kokko, B.; Loo, B. J. Am. Chem. Soc. 1986, 108, 6016.
5. (e) Guram, A. S.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
6. (f) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
7. (g) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
8. Synthesis of the aromatic amines by the reduction of aromatic azides is known. For some recent examples: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
9. (b) Benati, L.; Montevecci, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. Tetrahedron Lett. 1995, 36, 7313.
10. (c) Goulaouic-Dubois, C.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427.
11. (d) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254.
12. (e) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193. Huang, Y.; Zhang, Y.; Wang, Y. Tetrahedron Lett. 1997, 38, 1065.
13. (e) Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193. Huang, Y.; Zhang, Y.; Wang, Y. Tetrahedron Lett. 1997, 38, 1065.
14. (f) Kabalka, G.; Li, G. Tetrahedron Lett. 1997, 38, 5777.
15. (g) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796.
16. For example, see: Johnstone, R. A. W.; Wilby, A. H.; Entistle, I. D. Chem. Rev. 1985, 85, 129.
17. For example, see: Greenspoon, N.; Keinan, E. J. Org. Chem. 1988, 53, 3723.
18. For example, see: Rajagopal, S.; Spatola, A. F. J. Org. Chem. 1995, 56, 4481.
19. Bae, J. W.; Cho, Y. J.; Lee, S. H.; Yoon, C. M. Tetrahedron Lett. 2000, 41, 175.
20. Yasuhara, A.; Kasano, A.; Sakamoto, T. J. Org. Chem. 1999, 64, 2301.
21. Moody, C. J.; Pitts, M. R. Synlett 1998, 1028.
22. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243.
23. Boothroyd, S. R.; Kerr, M. A. Tetrahedron Lett. 1995, 36, 2411.
24. Kumbhar, P. S.; Sanchez-Valente, J.; Figueras, F. Tetrahedron Lett. 1998, 39, 2573.
25. Fisher, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393.
26. Suwinski, J.; Wagner, P.; Holt, E. M. Tetrahedron 1996, 52, 9541.
27. Becker, F. F.; Banik, B. K. Bioorg. Med. Chem. Lett. 1998, 8, 2877.
28. (a) Ghatak, A.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 3793.
29. (b) Banik, B. K., Zegrocka, O.; Banik, I.; Hackfeld, L.; Becker, F. F. Tetrahedron Lett. 1999, 40, 6731.
30. For an example, see: Han, B. H.; Boudjouk, P. J. Org. Chem. 1982, 47, 5030.
31. 18 at room temperature for 10-20 min (Table 1). The reaction started immediately as indicated by the evolution of gas, an increase in the internal temperature and by the change in the color of the mixtures. After the reaction was over, as indicated by TLC, water (5 mL) was added and then it was extracted with dichloromethane, dried over sodium sulfate and concentrated. The pure product was isolated by filtration through a short column over silica gel using ethyl acetate and hexanes as the solvent. The reaction can be carried out with 1-2 g nitro compound. All products have been characterized through a comparison of mp, TLC and NMR with authentic compounds.
32. A Bransonic Model 2210R-DTH was used for sonication.