Oxidative rearrangement of ketimines to amides by MCPBA and BF3·OEt2

Synlett

Volumn , Issue 1, 2003, Pages 112-114

  Kim, So Yeon ^a   An, Gwang Il ^a   Rhee, Hakjune ^a  

^a Hanyang University   (South Korea)

Author keywords

Amides; Ketimines; Ketones; Migratory aptitude; Oxidative rearrangement

Indexed keywords

AMIDE; BORON TRIFLUORIDE; IMINE; KETONE; NITROGEN; REAGENT;

ALKYLATION; AMIDATION; ANALYTIC METHOD; ARTICLE; ARYLATION; ELECTRON TRANSPORT; OXIDATION KINETICS; PRODUCTIVITY; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037243595     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (77)

1. For a list of methods, see: Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed.; Wiley-VCH: New York, 1999,; and references cited therein.
2. (a) Meshram, H. M. Synth. Commun. 1990, 20, 3253; and references cited therein.
3. (b) Bosch, A. I.; De La Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa, F. Synlett. 1995, 1295; and references cited therein.
4. (c) Srinivas, K. V. N. S.; Reddy, E. B.; Das, B. Synlett 2002, 625.
5. (d) Das, B.; Ravindranath, N.; Venkataiah, B.; Madhusudhan, P. J. Chem. Research, Synop. 2000, 482.
6. (e) Das, B.; Venkataiah, B. Synth. Commun. 1999, 29, 863.
7. (f) Das, B.; Madhusudhan, P.; Kashinatham, A. Tetrahedron Lett. 1998, 39, 431.
8. (g) Das, B.; Madhusudhan, P.; Kashinatham, A. Bioorg. Med. Chem. Lett. 1998, 8, 1403.
9. (h) Lavrent, A.; Jacquault, P.; Di Martino, J.-L.; Hamelin, J. J. Chem. Soc., Chem. Commun. 1995, 1101.
10. (i) Delgado, F.; Cano, A. C.; Garcia, O.; Alvarado, J.; Velasco, L.; Alvarez, C.; Rudler, H. Synth. Commun. 1992, 22, 2125.
11. (j) Barnett, C.; Cohn, I. M.; Lincoln, J. US Pat. 2754298, 1956; Chem. Abstr. 1957, 51, 2853.
12. (k) Novotny, A. US Pat. 2569114, 1951; Chem Abstr. 1952, 46, 5078.
13. (l) Novotny, A. US Pat. 2579851, 1951; Chem. Abstr. 1952, 46, 6668.
14. (a) Wolf, M. S.; Dutta, D.; Aube, J. J. Org. Chem. 1997, 62, 654.
15. (b) Kitagawa, O.; Vander Velde, D.; Dutta, D.; Morton, M.; Takusagawa, F.; Aube, J. J. Am. Chem. Soc. 1995, 117, 5169.
16. (c) Post, A. J.; Morrison, H. J. Am. Chem. Soc. 1995, 117, 7812.
17. (d) Aube, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009.
18. (e) Aube, J.; Wolf, M. S. Bioorg. Med. Chem. Lett. 1992, 2,925.
19. (f) Aube, J.; Wang, Y.; Ghosh, S.; Langhans, K. L. Synth. Commun. 1991, 21,693.
20. (g) Aube, J.; Hammond, M.; Gherardini, E.; Takusagawa, F. J. Org. Chem. 1991, 56, 499.
21. (h) Aube, J.; Hammond, M. Tetrahedron Lett. 1990, 31, 2963.
22. (i) Aube, J.; Wang, Y.; Hammond, M.; Tanol, M.; Takusagawa, F.; Vander Velde, D. J. Am. Chem. Soc. 1990, 112, 4879.
23. (j) Aube, J. Tetrahedron Lett. 1988, 29, 4509.
24. (k) Johnson, G. P.; Marples, B. A. J. Chem. Soc., Perkin Trans. 1 1988, 3399.
25. (l) Aube, J.; Burgett, P. M.; Wang, Y. Tetrahedron Lett. 1988, 29, 151.
26. (m) Johnson, G. P.; Marples, B. A. Tetrahedron Lett. 1985, 26, 4115.
27. (n) Oliveros, E.; Riviere et Armand Lattes, M. J. Heterocyclic Chem. 1980, 17, 1025.
28. (o) Oliveros, E.; Antoun, H.; Riviere et Armand Lattes, M. J. Heterocyclic Chem. 1976, 13, 623.
29. An, G.; Kim, M.; Kim, J. Y.; Rhee, H. Tetrahedron Lett., submitted.
30. 4 and concentrated by rotary-evaporation. The residue was purified by flash column chromatography (EtOAc/n-hexane = 1:1→5:1, v/v).
31. (a) Rozinov, V. G.; Dmitrichenko, M. Y.; Kolbina, V. E.; Dolgushin, G. V. Russ. J. Gen. Chem. 1999, 69, 1377.
32. (b) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979.
33. (c) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
34. (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Kutsuna, T.; Saigo, K. Tetrahedron Lett. 1998, 39, 1203.
35. (e) Lopez-Alvarado, P.; Avendano, C.; Menendez, J. C. J. Org. Chem. 1996, 61, 5865.
36. (f) Cozzi, P. G.; Veya, P.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Orgnometallics 1995, 14, 4092.
37. (g) Dharmasena, P. M.; Oliveira-Campos, A. M. F.; Raposo, M. M. M.; Shannon, P. V. R. J. Chem. Res., Synop. 1994, 296.
38. (h) Nussbaumer, P.; Dorfstaetter, G.; Grassberger, M. A.; Leitner, I.; Meingassner, J. G.; Thirring, K.; Stuetz, A. J. Med. Chem. 1993, 36, 2115.
39. (i) Lopez-Alvarado, P.; Avendano, C.; Menendez, J. C. Tetrahedron Lett. 1992, 33, 6875.
40. (j) Tsujimoto, M.; Hasegawa, K. JP Pat. JP02049756, 1990.
41. (k) Berthelot, M.; Helbert, M.; Laurence, C. Can. J. Chem. 1985, 63, 958.
42. (l) Urbanski, J.; Manek, M. B. Pol. J. Chem. 1983, 57, 603.
43. (m) Babudri, F.; Ciminale, F.; Di Nunno, L.; Florio, S. Tetrahedron 1982, 38, 557.
44. (n) Barbes, R.; Audebert, R.; Quivoron, C. J. Chim. Phys. Phys.-Chim. Biol. 1979, 76, 486.
45. (o) Freeman, H. S.; Butler, J. R.; Freedman, L. D. J. Org. Chem. 1978, 43, 4975.
46. (p) Wakselman, M.; Dome, M. Bull. Soc. Chim. Fr. 1975, 571.
47. (q) Birchall, J. M.; Clark, M. T. J. Chem. Soc., Perkin Trans. 1 1973, 1259.
48. (r) Fayat, C.; Foucaud, A. Bull. Soc. Chim. Fr. 1971, 3747.
49. (s) Welzel, P. Chem. Ber. 1970, 103, 1318.
50. (t) Wilshire, J. F. K. Tetrahedron Lett. 1968, 475.
51. (u) Chalapathi, V. V.; Ramiah, K. V. J. Mol. Spectrosc. 1968, 26, 444.
52. X-Ray crystallographic data for compounds 4b and 4e have been submitted for deposition at the Cambridge Crystallographic Data Center (CCDC 194994 and 194995).
53. (a) Marsh, A.; Nolen, E. G.; Gardinier, K. M.; Lehn, J. M. Tetrahedron Lett. 1994, 35, 397.
54. (b) Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1992, 33, 2027.
55. (c) Dessolin, M.; Eisenstein, O.; Golfier, M.; Prange, T.; Sautet, P. J. Chem. Soc., Chem. Commun. 1992, 132.
56. (d) Esser, F.; Brandt, K.; Pook, K. H.; Foerster, H. J.; Koeppen, H.; Leger, J. M.; Carpy, A. J. Chem. Soc., Perkin Trans. 1 1988, 3311.
57. (e) Kimura, M.; Okabayashi, I.; Isogai, K. J. Heterocyclic Chem. 1988, 25, 315.
58. (f) Suttle, N. A.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1983, 1369.
59. (g) Peterson, L. H.; Douglas, A. W.; Tolman, R. L. J. Heterocyclic Chem. 1981, 18, 659.
60. (h) Ramirez, F.; Telefus, C. D.; Prasad, V. A. V. Tetrahedron 1975, 31, 2007.
61. (i) Goldberg, V. D.; Harris, M. M. J. Chem. Soc., Perkin Trans. 2 1973, 1303.
62. (j) Shawali, A. S.; Hassaneen, H. M. Tetrahedron 1972, 28, 5903.
63. (k) McCullough, J. D. Jr.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1972, 94, 874.
64. (l) Fischer, H. P.; Funk-Kretschmar, F. Helv. Chim. Acta 1969, 52, 913.
65. (m) Wheeler, O. H.; Roman, F.; Santiago, M. V.; Quiles, F. Can. J. Chem. 1969, 47, 503.
66. (n) Relles, H. M. J. Org. Chem. 1968, 33, 2245.
67. (o) Bock, G. Chem. Ber. 1967, 100, 2870.
68. (p) Schulenberg, J. W.; Archer, S. In Organic Reactions, Vol. 14; Cope, A. C.; Adams, R.; Boekelheide, V.; Blatt, A. H.; Cairns, T. L.; Niemann, C., Eds.; John Wiley: New York, 1965, 1.
69. (a) Pellon, R. F.; Carrasco, R.; Marquez, T.; Mamposo, T. Tetrahedron Lett. 1997, 38, 5107.
70. (b) Pellon, R. F.; Mamposo, T.; Carrasco, R.; Rodes, L. Synth. Commun. 1996, 26, 3877.
71. (c) Pellon, R. F.; Carrasco, R.; Rodes, L. Synth. Commun. 1996, 26, 3869.
72. (d) Hanoun, J.-P.; Galy, J.-P.; Tenaglia, A. Synth. Commun. 1995, 25, 2443.
73. (e) Pellon, R. F.; Carrasco, R.; Millian, V.; Rodes, L. Synth. Commun. 1995, 25, 1077.
74. (f) Pellon, R. F.; Carrasco, R.; Rodes, L. Synth. Commun. 1993, 23, 1447.
75. (g) Lindley, J. Tetrahedron 1984, 40, 1433.
76. (h) Kaltenbronn, J. S.; Scherrer, R. A.; Short, F. W.; Jones, E. M.; Beatty, H. R.; Saka, M. M.; Winder, C. V.; Wax, J.; Williamson, W. R. N. Arzneim. Forsch. 1983, 33, 621.
77. Hebky, J.; Radek, O.; Kejha, J. Collect. Czech. Chem. Commun. 1958, 3988.