A new efficient route for the formation of quinoxaline N-oxides and N,N′-dioxides using HOF·CH3CN

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5761-5765

  Carmeli, Mira ^a   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS ACETONITRILE; OXYGEN-TRANSFER AGENT; QUINOXALINE DERIVATIVES; QUINOXALINE N-OXIDES;

ACETONITRILE; CHARGE TRANSFER; DERIVATIVES; FLUORINE; OXYGEN; REACTION KINETICS;

NITROGEN OXIDES;

ACETONITRILE; CARBADOX; CARBOXYLIC ACID DERIVATIVE; FLUORINE; QUINOXALINE DERIVATIVE; QUINOXALINE N,N' DIOXIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PROTEUS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SALMONELLA;

ACETONITRILES; FLUORINE; HYDROGEN; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXIDES; QUINOXALINES;

EID: 33746330771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0608016     Document Type: Article

References (32)

1. Haddadin, M. J.; Issidorides, C. H. Heterocycles 1976, 4, 767.
2. (a) Chas Pfizer and Co. U.S. Patent 1968, 3 371 090.
3. (b) Research Corp. U.S. Patent 1968. 3 398 141.
4. Haddadin, M. J.; Kattan, A. M. A.; Issidorides. C. H. J. Org. Chem. 1985, 50, 129.
5. Edwards, M. L.; Bambury, R. E.; Ritter, H. W. J. Med. Chem. 1976, 19, 330.
6. Kim, H. K. U.S. Patent 1972, 3 644 363.
7. (a) Issidorides, C. H.; Haddadin, M. J. J. Org. Chem. 1966, 3l, 4067.
8. (b) Kluge, A. F.; Maddox, M. L.; Lewis, G. S. J. Org. Chem. 1980, 45, 1909.
9. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocyclic N-Oxides: Academic Press: New York, 1971; Chapter 2.
10. (b) Cheeseman, G. W. H.; Werstiuk, E. S. G. Adv. Heterocycl. Chem. 1972, 14, 99.
11. Rozen, S.; Carmeli, M. J. Am. Chem. Soc. 2003, 125, 8118-8119.
12. Golan, E.; Rozen, S. J. Org. Chem. 2003, 68, 9170-9172.
13. Carmeli, M.; Rozen, S. Tetrahedron Lett. 2006, 47, 763.
14. (a) Rozen, S.; Dayan, S. Angew. Chem., Int. Ed. 1999, 38, 3471.
15. (b) Carmeli, M.; Rozen, S. J. Org. Chem. 2005, 70, 2131.
16. (a) Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457.
17. (b) Toyota, A.; Ono, Y.; Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 703.
18. Rozen, S.; Bareket, Y. J. Chem. Soc., Chem. Commun. 1994, 1959.
19. Amir, E.; Rozen, S. Angew. Chem., Int. Ed. 2005, 44, 7374.
20. Rozen, S. Eur. J. Org. Chem. 2005, 2433.
21. (a) Cooper, S. M.; Heaney, H.; Newbold, J. A.; Sanderson, W. R. Synlett 1990, 9, 533.
22. (b) Kobayashi, Y.; Kumadaki, I.; Sato, H.; Sekine, Y.; Hara, T. Chem. Pharm. Bull. 1974, 22, 2097.
23. Kol, M.; Rozen, S. J. Org. Chem. 1993, 58, 1593.
24. Nasielski, J.; Heilporn, S.; Nasielski-hinkens, R.; Geerts-Evrard, F. Tetrahedron 1987, 43, 4338.
25. Landouist, J. K.; Stacey, G. J. J. Chem. Soc. 1953, 282.
26. Mixan, C. E.; Pews, R. G. J. Org. Chem. 1977, 42, 1869.
27. Palamidessi, G.; Bernardi, L.; Farmaco, A. L. Ed. Sci. 1966, 21, 805.
28. Pollak, A.; Zupan, M.; Sket, B. Synthesis 1973, 495.
29. Chivers, G. E.; Suschitzky, H. Chem. Commun. 1971, 28.
30. Kyriacou, D. J. Heterocycl. Chem. 1971, 8, 697.
31. Tolstikov, G. A.; Jemilev, U. M.; Jurjev, V. P.; Gershanov, F. B.; Rafikov, S. R. Tetrahedron. Lett. 1971, 30, 2807.
32. Dayan, S.; Kol, M.; Rozen, S. Synthesis 1999, 1427.