Concerning the baker's yeast (Saccharomyces cerevisiae) mediated reduction of nitroarenes and other N-O containing functional groups

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3043-3046

  Blackie, Josie A ^a   Turner, Nicholas J ^a   Wells, Andrew S ^b  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; NITROBENZENE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; REACTION ANALYSIS; REDUCTION; SACCHAROMYCES CEREVISIAE;

EID: 0030938483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00504-2     Document Type: Article

References (18)

1. a) Davey, C.L.; Powell, L.W.; Turner, N.J.; Wells, A. Tetrahedron Lett., 1994, 35, 7867;
2. b) Takeshita, M.; Yoshida, S.; Kiya, R.; Higuchi, N.; Kobayashi, Y. Chem. Pharm. Bull., 1989, 37, 615;
3. c) Takeshita, M.; Yoshida, S. Heterocycles, 1990, 31, 2201;
4. d) Kamal, A; J. Org. Chem., 1991, 56, 2237;
5. e) Baik, W.; Han, J.L.; Lee, K.C.; Kim, B.H.; Hahn, J.-T. Tetrahedron Lett., 1994, 35, 3965;
6. f) Baik, W.; Park, T.H. J. Org. Chem., 1995, 60, 5683.
7. a) Takeshita, M.; Yoshida, S.; Kohno, Y. Heterocycles, 1994, 37, 553;
8. b) Navarro-Ocaña, A.; Jiménez-Estrada, M.; González-Paredes, M.B.; Bárzana, E. Synlett, 1996, 695.
9. Baik, W.; Rhee, J.U.; Lee, S.H.; Lee, N.H.; Kim, B.H.; Kim, K.S.; Tetrahedron Lett., 1995, 36, 2793.
10. Bianchi, G.; Comi, G.; Venturini, I. Gazz. Chim. Ital., 1984, 114, 285; Easton, C.J.; Hughes, C.M.; Kirby, K.D.; Savage, G.P.; Simpson, G.W.; Tiekink, E. R. T. J. Chem. Soc., Chem. Commun., 1994, 2035.
11. Bianchi, G.; Comi, G.; Venturini, I. Gazz. Chim. Ital., 1984, 114, 285; Easton, C.J.; Hughes, C.M.; Kirby, K.D.; Savage, G.P.; Simpson, G.W.; Tiekink, E. R. T. J. Chem. Soc., Chem. Commun., 1994, 2035.
12. a) Takeshita, M.; Yoshida, S. Heterocycles, 1990, 30, 871;
13. b) Baik, W.; Kim, D.I.; Koo, S.; Rhee, Shin, S.H.; Kim, B.H. Tetrahedron Lett., 1997, 38, 845.
14. Phenylhydroxylamine is relatively unstable but can be prepared and conveniently stored as its N,O-bis-acetyl derivative; Org. Syn., 1989, 67, 187.
15. Typical conditions for the baker's yeast reduction of nitroarenes: The baker's yeast purchased from Sigma (Sigma type II) was initially purified using the following procedure (N.B. this purification of commercially available baker's yeast has been found to result in cleaner product isolation). To a solution of acetone (11) at -20 °C was added baker's yeast (200-300g) and the suspension stirred gently for 20 minutes after which the acetone was removed by decanting and the procedure repeated with a further quantity of acetone (11). After the second washing the yeast was collected and dried. Acetone-washed baker's yeast (10g) was suspended in tap water (40 ml) and incubated at ∼32 °C for 1h, after which the substrate (100 mg) dissolved in DMSO or hot ethanol (∼5 ml) was added. The reaction was shaken at 32 °C, in an orbital shaker, and the conversion monitored by t.l.c. Upon completion of the reaction, the aqueous medium was saturated with NaCl and the pH adjusted to 8. The entire mixture was then continuously extracted overnight with chloroform after which the chloroform layer was washed, dried and evaporated to yield the crude product. Standard chromatographic procedures lead to the isolation of the aniline products.
16. Vogel's Textbook of Practical Organic Chemistry, 4th Ed., p. 724.; Prato, M.; Quintily, U.; Scaplo, L.; Scorrano, G. Bull. Chim. Soc. France, 1987, N1, 99.
17. Vogel's Textbook of Practical Organic Chemistry, 4th Ed., p. 724.; Prato, M.; Quintily, U.; Scaplo, L.; Scorrano, G. Bull. Chim. Soc. France, 1987, N1, 99.
18. For a discussion of the purported baker's yeast catalysed 1,3-dipolar cycloaddition reactions of nitrile oxides see Easton, C.J.; Hughes, M.M.; Tiekink, E.R.T.; Savage, G.P.; Simpson, G.W. Tetrahedron Lett., 1995, 36, 629.