An efficient and versatile one-pot Beckmann rearrangement of ketoximes using mesitylenesulfonyl chloride

Synthesis

Volumn , Issue 9, 2008, Pages 1351-1358

  Ramalingan, Chennan ^a   Park, Yong Tae ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Amides; Beckmann rearrangement; Diazepan 5 ones; Ketoximes; Lactams; Mesitylenesulfonyl chloride; Piperidin 4 one oximes

Indexed keywords

AMIDES; CONFORMATIONS; CYCLIC VOLTAMMETRY; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BECKMANN REARRANGEMENT; KETOXIMES; LACTAMS; MESITYLENESULFONYL CHLORIDE; PIPERIDIN-4-ONE OXIMES;

KETONES;

1 METHYL 2,7 DIPHENYL[1,4]DIAZEPAN 5 ONE; 1,3 DIMETHYL 2,7 DIPHENYL[1, 4]DIAZEPAN 5 ONE; 1,3,3 TRIMETHYL 2,7 DIPHENYL[1,4]DIAZEPAN 5 ONE; 1,3,5 TRIMETHYLBENZENE; 1,3,6 TRIMETHYL 2,7 DIPHENYL[1,4]DIAZEPAN 5 ONE; 3 ETHYL 1 METHYL 2,7 DIPHENYL[1,4]DIAZEPAN 5 ONE; 3 ISOPROPYL 1 METHYL 2,7 DIPHENYL[1,4]DIAZEPAN 5 ONE; ALKYL GROUP; AMIDE; AROMATIC HYDROCARBON; DIAZEPAN 5 ONE LACTAM DERIVATIVE; LACTAM DERIVATIVE; OXIME DERIVATIVE; PIPERIDIN 4 ONE OXIME; PIPERIDINE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; BECKMANN REARRANGEMENT; CHEMICAL STRUCTURE; METHODOLOGY; ONE POT SYNTHESIS; SPECTROMETRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 44049084962     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042948     Document Type: Article

References (39)

1. (a) Gawley, R. E. Org. React. 1988, 35, 1.
2. (b) Donaruma, L. G.; Heldt, W. Z. Org. React. 1960, 11, 1.
3. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311.
4. (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272.
5. (b) Furuya, Y.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 11240.
6. (a) Chandrasekhar, S.; Gopalaiah, K. Tetrahedron Lett. 2002, 43, 2455.
7. (b) Dongare, M. K.; Bhagwat, V. V.; Ramana, C. V.; Gurjar, M. K. Tetrahedron Lett. 2004, 45, 4759.
8. (c) Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, L. Tetrahedron Lett. 2004, 45, 3369.
9. (d) Li, D.; Shi, F.; Guo, S.; Deng, Y. Tetrahedron Lett. 2005, 46, 671.
10. (e) Kusama, H.; Yamashita, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 373.
11. (f) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505; and references cited therein.
12. (a) Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. Angew. Chem. Int. Ed. 1999, 38, 2910.
13. (b) Ikushima, Y.; Hatakeda, K.; Sato, M.; Sato, O.; Arai, M. Chem. Commun. 2002, 19, 2208.
14. (c) Boero, M.; Ikeshoji, T.; Liew, C. C.; Terakura, K.; Parrinello, M. J. Am. Chem. Soc. 2004, 126, 6280.
15. (a) Guo, S.; Deng, Y. Catal. Commun. 2005, 6, 225.
16. (b) Guo, S.; Du, Z.; Zhang, S.; Li, D.; Li, Z.; Deng, Y. Green Chem. 2006, 8, 296.
17. (a) Forni, L.; Fornasari, G.; Giordano, G.; Lucarelli, C.; Katovic, A.; Trifiro, F.; Perri, C.; Nagy, J. B. Phys. Chem. Chem. Phys. 2004, 6, 1842.
18. (b) Ghiaci, M.; Abbaspur, A.; Kalbasi, R. Appl. Catal., A 2005, 287, 83.
19. Ramalingan, C.; Park, Y.-T. J. Org. Chem. 2007, 72, 4536.
20. (a) Kelly, T. A.; McNeil, D. W.; Rose, J. M.; David, E.; Shih, C. K.; Grob, P. M. J. Med. Chem. 1997, 40, 2430.
21. (b) Tucker, H.; Le Count, D. J. Comprehensive Heterocyclic Chemistry II, Vol. 9; Newkome, G. R., Ed.; Elsevier: Oxford, 1996, 151 and 1039.
22. (c) Thurston, D. E. Molecular Aspects of Anticancer Drug-DNA Interactions; The Macmillan Press Ltd.: London, 1993, 54.
23. (d) Thurston, D. E.; Bose, D. S. Chem. Rev. 1994, 94, 433.
24. Ramalingan, C.; Park, Y.-T.; Kabilan, S. Eur. J. Med. Chem. 2006, 41, 683; and references cited therein.
25. 1H NMR spectrum, due to the 1,3-spatial proximity effect between the equatorial proton on C-5 and the oxygen of the oxime (Refer to references 10 and 12 for more details).
26. Cope, A. C.; Cotter, R. J.; Roller, G. G. J. Am. Chem. Soc. 1955, 77, 3590.
27. (a) Abraham, R. J.; Fisher, J.; Loftus, P. Introduction to NMR Spectroscopy; John Wiley: New York, 1988, 45.
28. (b) Cooper, J. W. Spectroscopic Techniques for Organic Chemists; John Wiley: New York, 1980, 45.
29. (a) Katritzky, A. R. Advances in Heterocyclic Chemistry, Vol. 36; Academic Press: New York, 1984, 42.
30. (b) Trager, W. F.; Lee, C. M.; Beckett, A. H. Tetrahedron 1967, 23, 365.
31. (c) Wiewiorowski, M.; Skolik, J.; Krueger, P. J. Tetrahedron 1968, 24, 5439.
32. Tamura, Y.; Fujiwara, H.; Sumoto, K.; Ikeda, M.; Kita, Y. Synthesis 1973, 215.
33. Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
34. Young, C. G.; Pauline, R.; Jenny, J.; Christian, M.; Carsten, B. Org. Lett. 2004, 6, 3293.
35. Chretien, J. M.; Zammattio, F.; Le Grognec, E.; Paris, M.; Cahingt, B.; Montavon, G.; Quintard, J. P. J. Org. Chem. 2005, 70, 2870.
36. Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416.
37. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
38. 1H NMR spectra were compared to those obtained from corresponding authentic samples.
39. Matallana, A.; Kruger, A. W.; Kingsbury, C. A. J. Org. Chem. 1994, 59, 3020.