A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7243-7246

  Banik, Bimal K ^a   Mukhopadhyay, Chhanda ^a   Venkatraman, M S ^a   Becker, Frederick F ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; AROMATIC NITRO COMPOUND; IODINE; SAMARIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; REDUCTION;

EID: 0032190805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01555-X     Document Type: Article

References (38)

1. 1. For some examples, see: ( a ) Pirie, D. K.; Welch, W. M.; Weeks, P. D.; Volkmann, R. A. Tetrahedron Lett. 1986, 27, 1549.
2. ( b ) Kempf, D. J.; Norbeck, D. W.; Codacovi, L. M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M. F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook, W., Jr.; Clement, J. J.; Plattner, J. J., Erickson, J. J. Med. Chem. 1990, 33, 2687.
3. ( c ) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y. J. Med. Chem. 1990, 33, 2707.
4. 2. For catalytic heterogenous hydrogenation, see: ( a ) Rylander, P. N. Hydrogenation Methods; Academic Press: New York, 1985; Chapter 8.
5. ( b ) Johnstone, R. A. W.; Wilby, A. H.; Entistle, I. D. Chem. Rev. 1985, 85, 129.
6. ( c ) Weir, J. R.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1980, 45, 4926.
7. ( d ) Tafesh, A. M.; Beller, M. Tetrahedron Lett. 1995, 36, 9305.
8. For catalytic homogeneous hydrogenation, see: ( a ) James, B. R. Homogeneous Hydrogenation, Wiley: New York, 1973.
9. ( b ) Greenspoon, N.; Keinan, E. J. Org. Chem. 1988, 53, 3723.
10. For catalytic transfer hydrogenation, see: ( a ) Weiner, H.; Blum, J.; Sasson, Y. J. Org. Chem. 1991, 56, 4481.
11. ( b ) Rajagopal, S.; Spatola, A. F. J. Org. Chem. 1995, 56, 4481.
12. 3. For example, see: ( a ) Coleman G. H.; Blomquist, R. F. J. Am. Chem. Soc. 1941, 63, 1692.
13. ( b ) Beak, P.; Kokko, B. J. Org. Chem. 1982, 47, 2822.
14. ( c ) Kokko B.; Beak P. Tetrahedron Lett. 1983, 24, 561.
15. ( d ) Beak, P. Basha A.; Kokko, B.; Loo, B. J. Am. Chem. Soc. 1986, 108, 6016.
16. ( e ) Guram, A. S.; Buchwald, S. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.
17. ( f ) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
18. ( g ) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
19. 4. Huang, Y.; Zhang, Y.; Wang, Y. Tetrahedron Lett. 1997, 38, 1065.
20. 5. ( a ) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714.
21. ( b ) Banik, B. K.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1997, 38, 5077.
22. ( c ) Banik, B. K.; Zegrocka, O.; Manhas, M. S.; Bose, A. K. Heterocycles 1997, 46, 173.
23. 6 For some recent examples: ( a ) Scriven, E. F. V.; Turnbull, K. Chem Rev. 1988, 88, 297.
24. ( b ) Benati, L.; Montevecci, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. Tetrahedron Lett. 1995, 36, 7313.
25. ( c ) Goulaouic-Dubois, C.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427.
26. ( d ) Capperucci, A.; Degl'Innocenti, A.; Funicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254.
27. ( e ) Baruah, M., Boruah, A.; Prajapati, D.; Sandhu, J. S. Synlett 1996, 1193.
28. ( f ) Kabalka, G.; Li G. Tetrahedron Lett. 1997, 38, 5777.
29. ( g ) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796.
30. 7. The explosion of azides in the presence of metal catalysts is reported, for example, see: Sanler, S. R. Organic Functional Group Preparation, Vol, Academic Press Inc. 1992; chapter 13.
31. 8. For some recent examples, see: ( a ) Molander, G. A. Chem. Rev. 1992, 92, 29.
32. ( b ) Hasegawa, E.; Curran, D. P. J. Org. Chem 1993, 58, 5008.
33. ( c ) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 6, 307.
34. ( d ) Zhang, Y.; Lin, R. Synth.Commun. 1987, 17, 329.
35. 9 Imamoto, T.; Ono, M. Chem. Lett. 1987, 501.
36. 10. Hou, Z., Fujiwara, Y.; Hiroshi, T. J. Org. Chem. 1988, 53, 3118.
37. 11. All products have been characterized through a comparison of mp, TLC and NMR with authentic compounds.
38. 12. Rudali, G.; Buu-Hoi, N. P.; Lacassagne, A. C. R. Acad. Sci. (Paris) 1953, 236, 2020.