Design and synthesis of 1-benzazepine derivatives by strategic utilization of Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis

European Journal of Organic Chemistry

Volumn , Issue 6, 2008, Pages 1054-1064

  Kotha, Sambasivarao ^a   Shah, Vrajesh R ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

1 benzazepine; Aza claisen rearrangement; Cross coupling; Metathesis

Indexed keywords

EID: 53649100112     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700921     Document Type: Article

References (74)

1. a) L. M. Fleeman, P. J. Irwin, P. A. Phillips, J. West, Aust Vet. J. 2000, 78, 825-830;
2. b) X. Wang, V. Gattone II, P. C. Harris, V. E. Torres, J. Am. Soc. Nephrol. 2005, 16, 846-851;
3. c) H. Ogawa, H. Yamashita, K. Kondo, Y. Yamamura, H. Miyamoto, K. Kan, K. Kitano, M. Tanaka, K. Nakaya, S. Namamura, T. Mori, M. Tominaga, Y. Yabuuchi, J. Med. Chem. 1996, 39, 3547-3555;
4. d) Y. Yamamura, H. Ogawa, H. Yamashita, T. Chihara, H. Miyamoto, S. Nakamura, T. Onogawa, T. Yamashita, T. Hosokawa, T. Mori, M. Tominaga, Y. Yabuuchi, Br. J. Pharmacol. 1992, 105, 787-791.
5. a) K. Kondo, H. Ogawa, H. Yamashita, H. Miyamoto, M. Tanaka, K. Nakaya, K. Kitano, Y. Yamamura, S. Nakamura, T. Onogawa, T. Mori, M. Tominaga, Biomed. Chem. Lett. 1999, 7, 1743-1754;
6. b) Y. Yamamura, S. Nakamura, S. Itoh, T. Hirano, T. Onogawa, T. Yamashita, Y. Yamada, K. Tsujimae, M. Aoyama, K. Kotosai, H. Ogawa, H. Yamashita, K. Kondo, M. Tominaga, G. Tsujimoto, T. Mori, J. Pharm. Exp. Ther. 1998, 287, 860-867.
7. R. L. Webb, D. Miller, V. Traina, H. J. Gomez, Cardiovascular Drug Rev. 1990, 8, 89-104.
8. J. C. Corbel, P. Uriac, J. Huet, C. A. E. Martin, C. Advenier, Eur. J. Med. Chem. 1995, 30, 3-13.
9. P. D. Leeson, L. L. Iversen, J. Med. Chem. 1994, 37, 4053-4067.
10. A. Hassner, B. Amit, V. Marks, H. E. Gottlieb, J. Org. Chem. 2003, 68, 6853-6858.
11. a) A. P. Guzikowski, E. R. Whittemore, R. M. Woodward, E. Weber, J. F. W. Keana, J. Med. Chem. 1997, 40, 2424-2429;
12. b) Y. Murakami, H. Hara, T. Okada, H. Hashizume, M. Kii, Y. Ishihara, M. Ishikawa, M. Shimamura, S. Mihara, G. Kato, K. Hanasaki, S. Hagishita, M. Fujimoto, J. Med. Chem. 1999, 42, 2621-2632;
13. c) C. Schultz, A. Link, M. Leost, D. W. Zaharevitz, R. Gussio, E. A. Sausville, L. Meijer, C. Kunick, J. Med. Chem. 1999, 42, 2909-2919;
14. d) Y. Aramaki, M. Seto, T. Okawa, T. Oda, N. Kanzaki, M. Shiraishi, Chem. Pharm. Bull. 2004, 53, 254-258;
15. e) C. Kunick, K. Lauenroth, K. Wieking, X. Xie, C. Schultz, R. Gussio, D. Zaharevitz, M. Leost, L. Meijer, A. Weber, F. S. Jørgensen, T. Lemcke, J. Med. Chem. 2004, 47, 22-36.
16. H. Plieninger, D. Wild, Chem. Ber. 1966, 99, 3070-3075.
17. T. Sakan, S. Matsubara, H. Takagi, Y. Tokunaga, T. Miwa, Tetrahedron Lett. 1968, 4925-4928.
18. G. Schroeter, A. Gluschke, S. Geotzky, J. Huang, G. Irmisch, E. Laves, O. Schrader, G. Stier, Ber. Dtsch. Chem. Ges. 1930, 63, 1308-1329.
19. a) L. H. Briggs, G. C. De Ath, J. Chem. Soc. 1937, 456-457;
20. b) R. W. Richard, R. M. Smith, Tetrahedron Lett. 1966, 7, 2361-2365;
21. c) K. I. Booker-Milburn, I. R. Dunkin, F. C. Kelly, A. I. Khalaf, D. A. Learmonth, G. R. Proctor, D. I. C. Scopes, J. Chem. Soc., Perkin Trans. 1 1997, 3261-3273.
22. a) A. Cromarty, G. R. Proctor, J. Chem. Soc. Chem. Commun. 1968, 842-843;
23. b) A. Cromarty, K. E. Hque, G. R. Proctor, J. Chem. Soc. C 1971, 3536-3540.
24. Y. Sato, H. Kojima, H. Shirai, J. Org. Chem. 1976, 41, 195-200.
25. Z. B. Zheng, P. Dowe, Tetrahedron Lett. 1993, 34, 7709-7712.
26. a) M. Quadir, R. E. Priestley, T. W. D. F. Rising, T. Gelbrich, S. J. Coles, M. B. Hursthouse, P. W. Sheldrake, N. Whittall, K. K. Hii, Tetrahedron Lett. 2003, 44, 3675-3678;
27. b) M. Quadir, J. Cobb, P. W. Sheldrake, N. Whittall, A. J. P. White, K. K. Hii, P. N. Horton, M. B. Hursthouse, J. Org. Chem. 2005, 70, 1545-1551;
28. c) M. Quadir, J. Cobb, P. W. Sheldrake, N. Whittall, A. J. P. White, K. K. Hii, P. N. Horton, M. B. Hursthouse, J. Org. Chem. 2005, 70, 1552-1557.
29. G. Dyker, H. Markwitz, Synthesis 1998, 1750-1754.
30. U. Martinez-Estibalez, N. Sotomayor, E. Lete, Tetrahedron Lett. 2007, 48, 2919-2922.
31. a) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110;
32. b) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956;
33. c) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
34. a) R. H. Grubbs (Ed.), Handbook of Metathesis, Wiley-VCH, Weinheim, 2003, vol. 1-3;
35. for some selected reviews on olefin metathesis, see: b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
36. Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
37. c) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
38. d) S. Kotha, N. Sreenivasachary, Indian J. Chem., Sect. B 2001, 40, 763-780;
39. e) S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968;
40. Angew. Chem. Int. Ed. 2003, 42, 1900-1923;
41. f) R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140;
42. g) M. D. McReynolds, J. M. Dougherty, P. R. Hanson, Chem. Rev. 2004, 104, 2239-2258;
43. h) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
44. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
45. a) A. Suzuki, H. C. Brown, Organic Synthesis via Boranes, Aldrich Chemical Company, Inc., Milwaukee, U.S.A., 2003, vol. 3;
46. for selected reviews on SM cross-coupling, see: b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
47. c) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695;
48. d) M. Moreno-Manas, R. Pleixats, R. M. Sebastian, A. Vallribera, A. Roglans, J. Organomet. Chem. 2004, 689, 3669-3684;
49. e) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563;
50. Angew. Chem. Int. Ed. 2005, 44, 4442-4489;
51. f) S. Kotha, K. Lahiri, Eur. J. Org. Chem. 2007, 1221-1236;
52. for a first paper on SM cross-coupling from our group, see: g) S. Kotha, K. Chakraborty, E. Brahmachary, Synlett 1999, 1621-1623.
53. For reports from our group on the use of combinations of SM cross-coupling and RCM, see: a) S. Kotha, K. Mandal, Eur. J. Org. Chem. 2006, 5387-5393;
54. b) S. Kotha, K. Mandal, K. K. Arora, V. R. Pedireddi, Adv. Synth. Catal. 2005, 347, 1215-1218;
55. for earlier work related to RCM and enyne metathesis from our group, see: c) S. Kotha, N. Sreenivasachary, Bioorg. Med. Chem. Lett. 1998, 8, 257-260;
56. d) S. Kotha, N. Sreenivasachary, E. Brahmachary, Tetrahedron Lett. 1998, 39, 2805-2808;
57. e) S. Kotha, S. Halder, E. Brahmachary, Tetrahedron 2002, 58, 9203-9208.
58. a) S. Kotha, K. Mandal, Tetrahedron Lett. 2004, 45, 2585-2588;
59. b) S. Kotha, V. R. Shah, K. Mandal, Adv. Synth. Catal. 2007, 349, 1159-1172.
60. S. Kotha, M. Behera, V. R. Shah, Synlett 2005, 1877-1880.
61. T. G. Back, M. Parvez, J. E. Wulff, J. Org. Chem. 2003, 68, 2223-2233.
62. G. Domínguez, L. Casarrubios, J. Rodríguez-Noriega, J. Pérez-Castells, Helv. Chim. Acta 2002, 85, 2856-2861.
63. A. C. Spivey, J. McKendrick, R. Srikaran, B. A. Helm, J. Org. Chem. 2003, 68, 1843-1851.
64. C. Escolano, K. Jones, Tetrahedron 2002, 58, 1453-1464.
65. For Pd-catalyzed 3-methylindole formation from N-alkenyl-2- haloanilines, see: a) R. Odle, B. Blevins, M. Ratcliff, L. S. Hegedus, J. Org. Chem. 1980, 45, 2709-2710;
66. b) R. C. Larock, S. Babu, Tetrahedron Lett. 1987, 28, 5291-5294.
67. a) U. Nubbemeyer in The Claisen Rearrangement (Eds.: M. Hiersemann, U. Nubbemeyer), Wiley-VCH, Weinheim, 2007, pp. 461-523;
68. for selected reports on aromatic aza-Claisen rearrangement, see: b) C. Pain, S. Célanire, G. Guillaumet, B. Joseph, Synlett 2003, 2089-2091;
69. c) K. C. Nicolaou, A. J. Roecker, R. Hughes, R. van Summeren, J. A. Pfefferkorn, N. Winssinger, Bioorg. Med. Chem. 2003, 11, 465-476;
70. d) W. K. Anderson, G. Lai, Synthesis 1995, 1287-1290.
71. T. Rosenau, A. Potthast, J. Röhrling, A. Hofinger, H. Sixta, P. Kosma, Synth. Commun. 2002, 32, 457-465.
72. G. W. Kabalka, L. Want, R. M. Pagni, Tetrahedron 2001, 57, 8017-8028.
73. Q. Zhang, X. Lu, X. Han, J. Org. Chem. 2001, 66, 7676-7684.
74. K. Knepper, S. Bräse, Org. Lett. 2003, 5, 2829-2832.