A novel strategy for the preparation of arylhydroxylamines: Chemoselective reduction of aromatic nitro compounds using bakers' yeast

Chemical Communications

Volumn , Issue 20, 2004, Pages 2338-2339

  Li, Feng ^a   Cui, Jingnan ^a   Qian, Xuhong ^a,b   Zhang, Rong ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; HYDROXYLAMINE; NITRO DERIVATIVE;

ARTICLE; BIOCATALYST; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

EID: 9144242647     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408566c     Document Type: Article

References (40)

1. (a) F. D. Sarlo, A. Brandi and P. Mascagni, Synthesis, 1981, 561;
2. (b) S. Toshiya, N. Masatomo and K. Shigekazu, J. Org. Chem., 1990, 55, 4221;
3. (c) R. S. Srivastava and K. M. Nicholas, J. Am. Chem. Soc., 1997, 119, 3302;
4. (d) H. C. Ming and L. T. Chu, New J. Chem., 2000, 24, 859;
5. (e) L. J. Lin, H. J. Sheng, Z. Z. Yuan, C. K. Kai and C. C. Ming, Chem.-Eur. J., 2001, 11, 2306;
6. (f) T. Hiroshi, T. J. Ichi, H. Suguru, T. Keisuke and O. Yoshinori, Eur. J. Org. Chem., 2003, 3920;
7. (g) G. Neri, G. Rizzo, C. Milone, J. D. Spence, A. E. Raymond and D. E. Norton, Tetrahedron Lett., 2003, 44, 849;
8. (h) T. Li, X. G. Yan, Y. Yong and L. L. Zu, Synthesis, 2003, 9, 1329.
9. (a) A. T. Balaban, R. E. Garrett, M. J. Lesko and W. A. Seitz, Org. Prep. Proced. Int., 1998, 30, 439;
10. (b) D. G. Smith, A. D. Gribble, D. Haigh, R. J. Ife, P. Lavery, P. Skett, B. P. Slingsby, F. W. Ward and A. West, Bioorg. Med Chem. Lett., 1999, 9, 3137;
11. (c) A. D. Mcgill, W. Zhang, J. Wittbrodt, J. Wang, H. B. Schlegel and P. G. Wang, Bioorg. Med. Chem., 2000, 8, 405;
12. (d) J. S. Yadav, B. V. S. Reddy and P. S. Sreedhar, Adv. Synth. Catal., 2003, 345, 564.
13. (a) C. L. M. Cobb, T. A. Connors, L. A. Elson, A. H. Khan, B. V. C. Mitchley, W. J. C. Ross and M. E. Whisson, Biochem. Pharmacol., 1969, 18, 1519;
14. (b) R. J. Knox, F. Friedlos, M. Jarman and J. J. Roberts, Biochem. Pharmacol., 1988, 37, 4661;
15. (c) R. J. Knox, F. Friedlos, T. Marchbank and J. Roberts, Biochem. Pharmacol., 1991, 42, 1691;
16. (d) G. M. Anlezark, R. G. Melton, R. F. Sherwood, W. R. Wilson, W. A. Denny, B. D. Palmer, R. J. Knox, F. Friedlos and A. Williams, Biochem. Pharmacol., 1995, 50, 609;
17. (e) E. Johansson, G. N. Parkinson, W. A. Denny and S. Neidle, J. Med. Chem., 2003, 46, 4009.
18. (a) O. Kamm, Org. Synth. Coll. Vol. 1, 1941, 445;
19. (b) K. Taya, Chem. Commun., 1966, 14, 464;
20. (c) I. D. Entwistle and T. Gilkerson, Tetrahedron, 1978, 34, 213;
21. (d) N. R. Ayyangar, K. C. Brahme, U. R. Kalkote and K. Y. Srinivasan, Synthesis, 1984, 938;
22. (e) K. Yanada, H. Yamaguchi, H. Meguri and S. Uchida, J. Chem. Soc., Chem. Commun., 1986, 1655.
23. (a) S. Servi, Synthesis, 1990, 1;
24. (b) R. Csuk and B. I. Glänzer. Chem. Rev., 1991, 91, 49.
25. (a) A. Kamal, M. V. Rao and A. B. Rao, Chem. Lett., 1990, 655;
26. (b) M. Takeshita and S. Yoshida, Heterocycles, 1990, 30, 871;
27. (c) D. E. Gibbs and D. Barnes, Tetrahedron Lett., 1990, 39, 5555;
28. (d) C. J. Easton, C. M. Hugher, K. D. Kirby, G. P. Savage, G. W. Sinpson and R. T. Tiekink, J. Chem. Soc., Chem. Commun., 1994, 2035;
29. (e) J. Tang, I. Brackenridge, S. Roberts, M. J. Beecher and A. J. Willets, Tetrahedron, 1995, 51, 13217;
30. (f) M. Baruah, A. Burua, D. Prajapati and J. S. Sandhu, Synlett, 1996, 1193;
31. (g) W. Baik, D. I. Kim, S. Koo, J. U. Rhee, S. H. Shin and B. H. Kim, Tetrahedron Lett., 1997, 38, 845;
32. (h) A. N. Ocaña, L. F. Olguín, H. Luna, M. J. Estrada and E. Bárzana, J. Chem Soc., Perkin Trans. 1, 2001, 2754.
33. (a) W. Baik, J. L. Han, K. C. Lee, N. H. Lee, B. H. Kim and J. T. Hahn, Tetrahedron Lett., 1994, 35, 3965;
34. (b) W. Baik, J. U. Rhee, S. H. Lee, N. H. Lee, B. H. Kim and K. S. Kim, Tetrahedron Lett., 1995, 36, 2793;
35. (c) W. Baik and T. H. Park, J. Org. Chem., 1995, 60, 5683;
36. (d) J. A. Blackie, N. J. Turner and A. S. Wells, Tetrahedron Lett., 1997, 38, 3043.
37. P. D. Arrigo, G. P. Fantoni and S. Servi, Adv. Appl. Microbiol., 1997, 44, 81.
38. (a) J. C. Spain, Annu. Rev. Microbiol., 1995, 49, 523;
39. (b) R. L. Koder, C. A. Haynes, M. E. Rodgers, D. W. Rodgers and A. F. Miller, Biochemistry, 2002, 4, 14197;
40. (c) I. T. Reeve and M. G. Miller, Chem. Res. Toxicol., 2002, 15, 352.