Reduction of aromatic nitro compounds using samarium metal in the presence of a catalytic amount of iodine under aqueous media

Synlett

Volumn , Issue 7, 1999, Pages 1065-1066

  Wang, Lei ^a   Zhou, Longhu ^a   Zhang, Yongmin ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Aqueous media; Aromatic amines; Aromatic nitro compounds; Reduction; Samarium metal

Indexed keywords

AMIDE; AMMONIUM CHLORIDE; AROMATIC AMINE; AROMATIC NITRO COMPOUND; HALOGEN; HYDRAZINE DERIVATIVE; IODINE; SAMARIUM;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032776932     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2788     Document Type: Article

References (23)

1. Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573; Molander, G. A. Chem. Rev. 1992, 92, 29; Molander, G. A. Organic Reaction 1994, 46, 211; Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
2. Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573; Molander, G. A. Chem. Rev. 1992, 92, 29; Molander, G. A. Organic Reaction 1994, 46, 211; Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
3. Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573; Molander, G. A. Chem. Rev. 1992, 92, 29; Molander, G. A. Organic Reaction 1994, 46, 211; Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
4. Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573; Molander, G. A. Chem. Rev. 1992, 92, 29; Molander, G. A. Organic Reaction 1994, 46, 211; Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
5. Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1997, 38, 3271; Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1996, 37, 9313; Lautens, M.; Delanghe, P. H. J. Org. Chem. 1995, 60, 2474.
6. Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1997, 38, 3271; Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1996, 37, 9313; Lautens, M.; Delanghe, P. H. J. Org. Chem. 1995, 60, 2474.
7. Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1997, 38, 3271; Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett. 1996, 37, 9313; Lautens, M.; Delanghe, P. H. J. Org. Chem. 1995, 60, 2474.
8. Hou, Z.; Takamine, K.; Fujiwara, Y. Chem. Lett. 1987, 305.
9. Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525; Clive, D, L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 3801.
10. Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525; Clive, D, L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 3801.
11. Wang, L.; Zhang, Y. Tetrahedron 1998, 54, 11129; Lautens, M.; Ren, Y. J. Org. Chem. 1996, 61, 2210.
12. Wang, L.; Zhang, Y. Tetrahedron 1998, 54, 11129; Lautens, M.; Ren, Y. J. Org. Chem. 1996, 61, 2210.
13. Wang, L.; Zhang, Y. Tetraheddron, Lett. 1998, 39, 5257.
14. Hou, Z.; Fujiwara. Y.; Taniguchi, H. J. Org, Chem. 1988, 53, 3118.
15. Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035.
16. Alper, H.; Amaratunga, S. Tetrahedron Lett. 1980, 21, 2603.
17. Suzuki, H.; Hanazaki, Y. Chem. Lett. 1986, 549.
18. Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393.
19. Boothroyd, S. R.; Kerr, M. A. Tetrahedron Lett. 1995, 36, 2411.
20. Upadhya, T. T.; Katdare, S. P.; Sabde, D. P.; Ramaswamy, V.; Sudalai, A. J. Chem. Soc., Chem. Commun. 1997, 1119.
21. Kumbhar, P. S.; Sanchez-Valente, J.; Figueras, F. Tetrahedron Lett. 1998, 39, 2573.
22. Moody, C. J.; Pitts, M. R. Synlett 1998, 1028.
23. 4Cl (aq., 0.5 mL) were added successively to it. The reaction mixture was stirred for the time indicated in Table at room temperature. The reaction was then quenched by the addition of HCl (1 mol/L, 2 mL). The mixture was extracted with ether (25 mL × 2). The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The product was isolated by preparative TLC on silica gel eluting with cyclohexane-ethyl acetate (3:1).