One-pot synthesis of aryl oxime analogues from methyl arenes using NBS and hydroxyl amine hydrochloride

Tetrahedron Letters

Volumn 53, Issue 21, 2012, Pages 2632-2635

  Chandrappa, S ^a   Umashankara, M ^a   Vinaya, K ^a,b   Ananda Kumar, C S ^a   Rangappa, K S ^a  

^a UNIVERSITY OF MYSORE   (India)

^b Government First Grade College   (India)

Author keywords

Aryl oximes; Benzoyl peroxide; Hydroxyl amine hydrochloride; Methyl arenes; N Bromo succinamide (NBS)

Indexed keywords

ESTER; HYDROXYL GROUP; HYDROXYLAMINE; METHYL GROUP; OXIME DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ONE POT SYNTHESIS; PURIFICATION;

TRIFLUORO;

EID: 84859762113     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.03.052     Document Type: Article

References (35)

1. S. Chandrasekhar, and K. Gopalaiah Tetrahedron Lett. 42 2001 8123 8125
2. C. Walter Jr. J. Am. Chem. Soc. 74 1952 5185 5187
3. H.Q. Li, Z.P. Xiao, Y. Luo, T. Yan, P.C. Lv, and H.L. Zhu Eur. J. Med. Chem. 44 2009 2246 2251
4. N. Anand, N.A. Owston, A.J. Parker, P.A. Slatforda, and J.M.J. Williamsa Tetrahedron Lett. 48 2007 7761 7763
5. B.A. Mendelsohn, S. Lee, S. Kim, F. Teyssier, V.S. Aulakh, A. Marco, and M.A. Ciufolini Org. Lett. 11 2009 1539 1542
6. A. Pohjakallio, and P.M. Pihko Chem. Eur. J. 15 2009 3960 3964
7. R.G. Shotter, D. Sesardi, and P.H. Wright Tetrahedron 31 1975 3069 3072
8. K. Parthasarathy, and C.H. Cheng J. Org. Chem. 74 2009 9363
9. P.C. Too, Y.F. Wang, and S. Chiba Org. Lett. 12 2010 568 5691
10. P. Chaudhuri Coord. Chem. Rev. 243 2003 143 190
11. V.Y. Kukushikin, and A.J.L. Pombeiro Coord. Chem. Rev. 181 1999 147 175
12. V.Y. Kukushikin, D. Tudela, and A.J.L. Pombeiro Coord. Chem. Rev. 156 1996 333 362
13. G.A. Olah, P. Ramaiah, C.S. Lee, and G.K. Suryaprakash Synlett 1992 337 339
14. D.C. Iffland, G.X. Criner, M. Koral, F.J. Lotspeich, Z.B. Papanastassiou, and S.M. White Jr. J. Am. Chem. Soc. 75 1953 4044 4048
15. H. Iwamura J. Med. Chem. 23 1980 308 312
16. Y. Takahashi, Y. Miyashita, Y. Tanaka, H. Abe, and S. Sasaki J. Med. Chem. 25 1982 1245 1248
17. P.A. Eyer, and F. Worek T.C. Marrs, R.L. Maynard, F.R. Sidell, Chemical Warfare Agents Toxicology and Treatment 2007 Wiley 305 329
18. A. Atria, and M. Michael Pharmazie 37 1982 551 553
19. A. Nakayama, H. Iwamura, A. Niwa, Y. Nakagawa, and T. Fujita J. Agric. Food Chem. 33 1985 1034 1041
20. J.P. Ley, and H.J. Bertram Eur. J. Lipid Sci. Technol. 104 2002 319 323
21. M. Kato, S. Nishino, M. Ohno, S. Fukuyama, Y. Kita, Y. Hirasawa, Y. Nakanishi, H. Takasugi, and K. Sakane Bioorg. Med. Chem. Lett. 6 1996 33 38
22. R.W. Hartmann, M. Hector, S. Haidar, P.B. Ehmer, W. Reichert, and J. Jose J. Med. Chem. 43 2000 4266 4277
23. E. Beckman Chem. Ber. 23 1890 1680 1692
24. A.I. Vogel Text Book of Practical Organic Chemistry 1986 Longman 1113
25. W.K. Slater J. Chem. Soc. 117 1920 587 590
26. W.H. Hartung, and J.C. Munch J. Am. Chem. Soc. 51 1929 2262 2266
27. V.J. Braun, and W. Sobecki Chem. Ber. 44 1911 2526 2534
28. J.R. Hanson, and E. Premuzic Tetrahedron 23 1967 4105 4110
29. A.I. Vogel Text Book of Practical Organic Chemistry 1986 Longman New York 1113
30. K. Weissermer, and H.J. Arpe Industrial Organic Chemistry 1978 Springer Verlag
31. U.S. Patent 4,794,198, 1988.
32. M.A. Mantegazza, A. Cesana, and M. Pastori Chem. Ind. 68 1996 97 106
33. U.S. Patent 4,163,756, 1979.
34. S. Chandrappa, C.S. Ananda Kumara, and K.S. Rangappa Tetrahedron Lett. 42 2010 6493 6497
35. S. Chandrappa, K. Vinaya, U. Muddegowda, and K.S. Rangappa Tetrahedron Lett. 52 2011 5474 5477