Heterogeneous N-oxidation of pyridines using a combined oxidant of hydrogen peroxide and nitriles catalysed by basic hydrotalcites

New Journal of Chemistry

Volumn 23, Issue 8, 1999, Pages 799-801

  Yamaguchi, Kazuya ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZONITRILE; HYDROGEN PEROXIDE; HYDROTALCITE; NITRILE; PYRIDINE DERIVATIVE;

ARTICLE; CALORIMETRY; CATALYSIS; CATALYST; CHEMICAL REACTION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032783037     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904446i     Document Type: Article

References (27)

1. (a) K. Kaneda, S. Ueno and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797.
2. (b) K. Kaneda, S. Ueno and T. Imanaka, J. Mol. Catal., 1995, 102, 135.
3. (c) K. Kaneda and T. Yamashita, Tetrahedron Lett., 1996, 37, 4555.
4. (d) S. Ueno, K. Ebitani, A. Ookubo and K. Kaneda, Appl. Surf. Sci., 1997, 121/122, 366.
5. K. Kaneda, T. Yamashita, T. Matsushita and K. Ebitani, J. Org. Chem., 1998, 63, 1750.
6. T. Matsushita, K. Ebitani and K. Kaneda, Chem. Commun., 1999, 265.
7. (a) S. Ueno, K. Yamaguchi, K. Yoshida, K. Ebitani and K. Kaneda, Chem. Commun., 1998, 295.
8. (b) K. Yamaguchi, K. Ebitani and K. Kaneda, J. Org. Chem., 1999, 64, 2966.
9. (a) G. B. Payne, P. H. Deming and P. H. Williams, J. Org. Chem., 1961, 26, 651.
10. (b) G. B. Payne, J. Org. Chem., 1961, 26, 668.
11. (c) D. C. Edwards, Tetrahedron Lett., 1966, 4767.
12. (d) E. Ochiai, Aromatic Amine Oxides, Elsevier, Amsterdam, 1967.
13. (e) G. E. Chivers and H. Suschitzky, J. Chem. Soc., Chem. Commun., 1971, 28.
14. (a) R. A. Sheldon, CHEMTECH, 1994, March, 38.
15. (b) P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
16. (c) J. H. Clark, Green Chem., 1999, 1, 1.
17. (a) K. Takabe, T. Yamada and T. Katagiri, Chem. Lett., 1982, 1987.
18. (b) R. W. Murray and K. Iyanar, J. Org. Chem., 1996, 61, 8099.
19. (c) A. Goti and L. Nannelli, Tetrahedron Lett., 1996, 37, 6027.
20. (d) C. Copéret, H. Adolfsson, T. V. Khuong, A. K. Yudin and K. B. Sharpless, J. Org. Chem., 1998, 63, 1740.
21. (e) C. Copéret, H. Adolfsson, J. P. Chiang, A. K. Yudin and K. B. Sharpless, Tetrahedron Lett., 1998, 39, 761.
22. (a) S. Miyata, Clays Clay Miner., 1980, 28, 50.
23. (b) F. Cavani, F. Trifirò and A. Vaccari, Catal. Today, 1991, 11, 173.
24. By contrast, use of the MTO catalyst resulted in 91% yield of di-N-oxide.
25. 2-Chloropyridine and 2-phenylpyridine afforded the corresponding N-oxides in 17 and 63% yields, respectively, under the same reaction conditions as in Table 2.
26. For this substrate, the resultant reaction mixture was poured into ethyl acetate, which was extracted with water. After removal of water, 0.57 g (87%) of quinoline N-oxide monohydrate was obtained.
27. 2, benzamide could be easily regenerated to benzonitrile.