A simple and efficient method for the preparation of pyridine-N-oxides II

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 761-764

  Copéret, Christophe ^a   Adolfsson, Hans ^a   Chiang, Jay P ^a   Yudin, Andrei K ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(TRIMETHYLSILYL)PEROXIDE; PEROXIDE; PYRIDINE 1 OXIDE; PYRIDINE DERIVATIVE; RHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DISTILLATION; FILTRATION; NONHUMAN; OXIDATION; TECHNIQUE;

EID: 0032546074     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10619-0     Document Type: Article

References (31)

1. 1. C. Copéret, H. Adolfsson, T.-A. V. Khuong, A. K. Yudin, K. B. Sharpless, submitted for publication.
2. 2. a) For the preparation of BTSP, see: P. G. Cookson, A. Davies, N. Fazal J. Organometal. Chem. 1975, 99, C31, M. Taddei, A. Ricci Synthesis 1986, 633;
3. 2. a) For the preparation of BTSP, see: P. G. Cookson, A. Davies, N. Fazal J. Organometal. Chem. 1975, 99, C31, M. Taddei, A. Ricci Synthesis 1986, 633;
4. b) for convenient large scale syntheses of BTSP: W. P. Jackson Synlett. 1990, 536; P. Dembech, A. Ricci, G. Seconi, M. Taddei Org. Synth. 1997, 74, 84; J. P. Chiang, K. B. Sharpless, manuscript in preparation.
5. b) for convenient large scale syntheses of BTSP: W. P. Jackson Synlett. 1990, 536; P. Dembech, A. Ricci, G. Seconi, M. Taddei Org. Synth. 1997, 74, 84; J. P. Chiang, K. B. Sharpless, manuscript in preparation.
6. b) for convenient large scale syntheses of BTSP: W. P. Jackson Synlett. 1990, 536; P. Dembech, A. Ricci, G. Seconi, M. Taddei Org. Synth. 1997, 74, 84; J. P. Chiang, K. B. Sharpless, manuscript in preparation.
7. 3. a) C. Copéret, H. Adolfsson, K. B. Sharpless Chem. Commun. 1997, 1565;
8. b) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless J. Am. Chem. Soc. 1997, 119, 6185.
9. 4. A. K. Yudin, K. B. Sharpless J. Am. Chem. Soc. in press.
10. 5. a) For a review on oxidation of pyridines, see: E. Ochiai, Aromatic Amine Oxides, Elsevier, Amsterdam 1967; A. Albini, S. Pietra Heterocyclic N-Oxides, CRC Press, 1991;
11. 5. a) For a review on oxidation of pyridines, see: E. Ochiai, Aromatic Amine Oxides, Elsevier, Amsterdam 1967; A. Albini, S. Pietra Heterocyclic N-Oxides, CRC Press, 1991;
12. b) for some examples of N-oxidation using peracids: Edwards, D. C. Gillespie Tetrahedron Lett. 1966, 4867;
13. c) for oxidation with a combination of hydrogen peroxides and acids/anhydrides: G. E. Chivers, H. Suschitzky J. Chem. Soc., Chem. Comm., 1971, 28; K. Takabe, T. Yamada, T. Katagiri Chem. Lett. 1982, 1987; V. Tortorella J. Chem. Soc., Chem. Comm., 1966, 308; Kaczmarek, R. Balicki, P. Nantka-Namirski Chem. Ber. 1992, 125, 1965;
14. c) for oxidation with a combination of hydrogen peroxides and acids/anhydrides: G. E. Chivers, H. Suschitzky J. Chem. Soc., Chem. Comm., 1971, 28; K. Takabe, T. Yamada, T. Katagiri Chem. Lett. 1982, 1987; V. Tortorella J. Chem. Soc., Chem. Comm., 1966, 308; Kaczmarek, R. Balicki, P. Nantka-Namirski Chem. Ber. 1992, 125, 1965;
15. c) for oxidation with a combination of hydrogen peroxides and acids/anhydrides: G. E. Chivers, H. Suschitzky J. Chem. Soc., Chem. Comm., 1971, 28; K. Takabe, T. Yamada, T. Katagiri Chem. Lett. 1982, 1987; V. Tortorella J. Chem. Soc., Chem. Comm., 1966, 308; Kaczmarek, R. Balicki, P. Nantka-Namirski Chem. Ber. 1992, 125, 1965;
16. c) for oxidation with a combination of hydrogen peroxides and acids/anhydrides: G. E. Chivers, H. Suschitzky J. Chem. Soc., Chem. Comm., 1971, 28; K. Takabe, T. Yamada, T. Katagiri Chem. Lett. 1982, 1987; V. Tortorella J. Chem. Soc., Chem. Comm., 1966, 308; Kaczmarek, R. Balicki, P. Nantka-Namirski Chem. Ber. 1992, 125, 1965;
17. d) for oxidation with DMDO: R. W. Murray, R. Jeyaraman J. Org. Chem. 1985, 50, 2847;
18. e) for some examples of transition metal catalyzed oxidation of pyridines: G. A. Tolstikov, U. M. Jemilev, V. P. Jurjev, P. B. Gershanov, S. R. Rafikov Tetrahedron Lett. 1971, 2807; C. J. Cabre, C. A. Palomo, Afinidad 1988, 45, 5111 [Chem. Abstr. 1989, 111, 77817];
19. e) for some examples of transition metal catalyzed oxidation of pyridines: G. A. Tolstikov, U. M. Jemilev, V. P. Jurjev, P. B. Gershanov, S. R. Rafikov Tetrahedron Lett. 1971, 2807; C. J. Cabre, C. A. Palomo, Afinidad 1988, 45, 5111 [Chem. Abstr. 1989, 111, 77817];
20. e) for some examples of transition metal catalyzed oxidation of pyridines: G. A. Tolstikov, U. M. Jemilev, V. P. Jurjev, P. B. Gershanov, S. R. Rafikov Tetrahedron Lett. 1971, 2807; C. J. Cabre, C. A. Palomo, Afinidad 1988, 45, 5111 [Chem. Abstr. 1989, 111, 77817];
21. 2 in the presence of 8 mol% MTO: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1996, 37, 805;
22. g) For reports on the MTO-catalyzed oxidations of amines and anilines: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1995, 36, 6415; Z. Zhu, J. H. Espenson J. Org. Chem. 1995, 60, 7728; see 3f; A. Goti, L. Nanelli Tetrahedron Lett. 1996, 37, 6025; R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing J. Org. Chem. 1996, 61, 8099; S. Yamazaki Bull. Soc. Chem. Jpn. 1997, 70, 877.
23. g) For reports on the MTO-catalyzed oxidations of amines and anilines: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1995, 36, 6415; Z. Zhu, J. H. Espenson J. Org. Chem. 1995, 60, 7728; see 3f; A. Goti, L. Nanelli Tetrahedron Lett. 1996, 37, 6025; R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing J. Org. Chem. 1996, 61, 8099; S. Yamazaki Bull. Soc. Chem. Jpn. 1997, 70, 877.
24. g) For reports on the MTO-catalyzed oxidations of amines and anilines: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1995, 36, 6415; Z. Zhu, J. H. Espenson J. Org. Chem. 1995, 60, 7728; see 3f; A. Goti, L. Nanelli Tetrahedron Lett. 1996, 37, 6025; R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing J. Org. Chem. 1996, 61, 8099; S. Yamazaki Bull. Soc. Chem. Jpn. 1997, 70, 877.
25. g) For reports on the MTO-catalyzed oxidations of amines and anilines: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1995, 36, 6415; Z. Zhu, J. H. Espenson J. Org. Chem. 1995, 60, 7728; see 3f; A. Goti, L. Nanelli Tetrahedron Lett. 1996, 37, 6025; R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing J. Org. Chem. 1996, 61, 8099; S. Yamazaki Bull. Soc. Chem. Jpn. 1997, 70, 877.
26. g) For reports on the MTO-catalyzed oxidations of amines and anilines: R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing Tetrahedron Lett. 1995, 36, 6415; Z. Zhu, J. H. Espenson J. Org. Chem. 1995, 60, 7728; see 3f; A. Goti, L. Nanelli Tetrahedron Lett. 1996, 37, 6025; R. W. Murray, K. Iyanar, J. Chen., J. T. Wearing J. Org. Chem. 1996, 61, 8099; S. Yamazaki Bull. Soc. Chem. Jpn. 1997, 70, 877.
27. 6. In contrast to the epoxidation of alkenes, the oxidation of pyridines might not require the presence of water as pyridines themselves could assist the activation of BTSP by Re catalysts. It is however difficult to disprove that trace amounts of water would be enough to perform this activation.
28. 2O.
29. 8. For a review on the use of N-oxides, see: 5a; A. K. Katritzky, C. W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon Press, Vol. 2, 1984.
30. 9. N-oxides, that are liquid or low melting, and the hexamethylsiloxane (formed concomitantly) are not miscible, which causes phase separation.
31. 2, see W. A. Herrmann, F. E. Kühn Acc. Chem. Res. 1997, 30, 169 and references cited therein.