Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1126-1136

  Hiroya, Kou ^a   Itoh, Shin ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHARGE TRANSFER; COPPER COMPOUNDS; SALTS; SYNTHESIS (CHEMICAL);

SEQUENTIAL CYCLIZATION REACTIONS; TRICYCLIC RING SYSTEMS;

AROMATIC HYDROCARBONS;

1 (4 TOLYL)SULFONYL DERIVATIVE; 1 METHYLSULFONYLINDOLE DERIVATIVE; 2 ETHYNYLANILINE DERIVATIVE; ALKALOID DERIVATIVE; ANILINE DERIVATIVE; COPPER ACETATE; COPPER ION; HIPPADINE; INDOLE; INDOLE DERIVATIVE; LYCORINE; NATURAL PRODUCT; POTASSIUM DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

ACETYLENE; ALKALOIDS; AMARYLLIDACEAE ALKALOIDS; ANILINE COMPOUNDS; BIOLOGICAL FACTORS; COPPER; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE;

EID: 1242352490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035528b     Document Type: Article

References (65)

1. (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
2. (b) Gribble, G. W. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Ed.; Pergamon Press: Oxford, UK, 1996;, Vol. 2, p 207.
3. (a) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507.
4. (b) Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Pérez, M.; García-Martín, M. A.; González, J. M. J. Org. Chem. 1996, 61, 5804.
5. (c) Kondo, Y.; Kojima, S.; Sakamoto, T. Heterocycles 1996, 43, 2741.
6. (d) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856.
7. (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
8. (b) Arcadi A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647.
9. (c) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687.
10. Recent review for palladium-catalyzed cyclization reactions, see: Larock, R. C., J. Organomet. Chem. 1999, 576, 111.
11. (a) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
12. (b) Esseveldt, B. C. J.; Delft, F. L.; Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717.
13. (c) Kamijo S.; Yamamoto Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
14. (d) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662.
15. (e) Yu, M. S.; Leon, L. L.; McGguire, M. A.; Botha, G. Tetrahedron Lett. 1998, 39, 9347.
16. (f) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
17. (g) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289.
18. (h) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305.
19. (i) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
20. (a) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35, 1823.
21. (b) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 1845.
22. (c) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 31.
23. Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529.
24. (a) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid B.; Knochel, P. Tetrahedron 2003, 59, 1571.
25. (b) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P.Angew. Chem., Int. Ed. 2000, 39, 2488.
26. (c) Dai, W. M.; Sun, L. P.; Guo, D. S. Tetrahedron Lett. 2002, 43, 7699.
27. (d) Dai, W. M.; Guo, D. S.; Sun, L. P. Tetrahedron Lett. 2001, 42, 5275.
28. For review, see: Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671.
29. (a) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001.
30. (b) Iritani, K.; Matsubara, S.; Uchimoto, K. Tetrahedron Lett. 1988, 29, 1799.
31. (a) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
32. (b) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
33. Yasuhara, A.; Kaneko, M.; Sakamoto, T. Heterocycles 1998, 48, 1793.
34. (a) Cacchi, S.; Fabrizi, G.; Pace, P.; Marinelli, F. Synlett 1999, 620.
35. (b) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803.
36. (a) Dai, W.-M.; Guo, D.-S.; Sun, L.-P.; Huang, X.-H. Org. Lett. 2003, 5, 2919.
37. (b) Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011.
38. For review, see: (c) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885.
39. Only a limited number of examples for unsubstituted aniline cyclization reactions have been reported. See refs 3c, 5b,d-f, 8, and 10b.
40. Part of this work has been communicated previously: Hiroya, K.; Itoh, S. ; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
41. Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841.
42. 2 (X = Cl or Br) have been reported: (a) Ma, S.; Xie, H. Org. Lett. 2000, 2, 3801.
43. (b) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314.
44. Arduini, A. L.; Garnett, M.; Thompson, R. C.; Wong, T. C. T. Can. J. Chem. 1975, 53, 3812.
45. (a) Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; John Wiley & Sons: NewYork, 1999; p 870.
46. 2O: Karpova, E. V.; Boltalin, A. I.; Zakharov, M. A.; Sorokina, N. I.; Korenev, Y. M. Z. Anorg. Allg. Chem. 1998, 624, 741.
47. 2O: Kiriyama, R.; Ibamoto, H.; Matsuo, K. Acta Crystallogr. 1954, 7, 482.
48. The same observation has been reported for the solid-phase reaction. See ref 14a.
49. Ghosal, S.; Rao, P. H.; Jaiswal, D. K.; Kumar, Y.; Frahm, A. W. Phytochemistry 1981, 20, 2003.
50. (a) Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899.
51. (b) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120.
52. (c) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595.
53. (d) Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300.
54. (e) Miki, Y.; Shirokoshi, H.; Matushita, K. Tetrahedron Lett. 1999, 40, 4347.
55. (f) Hutchings, R. H.; Meyers, I. A. J. Org. Chem. 1996, 61, 1004.
56. (g) Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. R.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551.
57. (h) Sakamoto, T.; Yasuhara, A.; Kondo, Y.; Yamanaka, H. Heterocycles 1993, 36, 2597.
58. (i) Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1991, 32, 3859.
59. (j) Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523.
60. (k) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1987, 28, 5895.
61. Krimen, L. I. Organic Syntheses; Wiley: New York, 1988; Collect Vol. VI, p 8.
62. (a) Banwell, M. G.; Havey, J. E.; Hockless, D. C. R. J. Org. Chem. 2000, 65, 4241.
63. (b) Banwell, M. G.; Cowden, C. J.; Gable, R. W. J. Chem. Soc., Perkin Trans. 1 1994, 3515.
64. Smith, A. B.; Visnick, M.; Haseltine, J. N.; Sprengeler, P. L. Tetrahedron 1986, 42, 2957.
65. Fleming, I.; Farckenpohl, J.; Ila, H. J. Chem. Soc., Perkin Trans. 1 1998, 1229.