Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis

Angewandte Chemie - International Edition

Volumn 52, Issue 4, 2013, Pages 1266-1269

  Zhan, Fuxu ^a   Liang, Guangxin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

C N coupling; copper; heterocycles; natural products; synthetic methods

Indexed keywords

C-N COUPLING; FISCHER INDOLE SYNTHESIS; HETEROCYCLES; INDOLIZATION; NATURAL PRODUCTS; SELECTIVE SYNTHESIS; STRUCTURAL MOTIFS; SYNTHETIC METHODS; VINYL HALIDES;

CATALYSIS; CHEMISTRY; COPPER;

REGIOSELECTIVITY;

ALKALOID; COPPER; INDOLE; INDOLE DERIVATIVE; PHENYLHYDRAZINE DERIVATIVE; VINCA ALKALOID; VINCORINE; VINYL BROMIDE; VINYL DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; COPPER; INDOLES; PHENYLHYDRAZINES; STEREOISOMERISM; VINCA ALKALOIDS; VINYL COMPOUNDS;

EID: 84872410404     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207173     Document Type: Article

References (78)

1. R. J. Sundberg, Indoles, Academic Press, London, 1996
2. A. Rahman, Indole Alkaloids, Harwood Academic Publisher, Amsterdam, 1998
3. "Indole and its Derivatives":, A. Joule, in Science of Synthesis: Methods of Molecular Transformations (Houben-Weyl), Cat. 2, Vol. 10 (Eds.:, E. J. Thomas,), Thieme, Stuttgart, 2000, p. 361
4. T. Eicher, S. Hauptmann, in The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, 2 nd ed., Wiley-VCH, Weinheim, 2003.
5. D. F. Taber, P. K. Tirunahari, Tetrahedron 2011, 67, 7195-7210
6. S. Cacchi, G. Fabrizi, A. Goggiamani, Org. React. 2012, 76, 281-534.
7. E. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 1883, 16, 2241-2245
8. E. Fischer, O. Hess, Ber. Dtsch. Chem. Ges. 1884, 17, 559-568.
9. D. L. Hughes, Org. Prep. Proced. Int. 1993, 25, 607-632
10. R. S. Downing, P. J. Kunkeler, in The Fischer Indole Synthesis (Eds.:, R. A. Sheldon, H. Bekkum,), Wiley-VCH, New York, 2001
11. J.-Z. Jiang, Y. Wang, Chin. J. Org. Chem. 2006, 26, 1025-1030.
12. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 6621-6622
13. B. P. Bondzic̈, P. Eilbracht, Org. Lett. 2008, 10, 3433-3436
14. I.-K. Park, S.-E. Suh, B.-Y. Lim, C.-G. Cho, Org. Lett. 2009, 11, 5454-5456
15. B. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel, Angew. Chem. 2010, 122, 9703-9706
16. Angew. Chem. Int. Ed. 2010, 49, 9513-9516
17. N. T. Patil, A. Konala, Eur. J. Org. Chem. 2010, 6831-6839
18. M. Inman, C. J. Moody, Chem. Commun. 2011, 47, 788-790
19. D. McAusland, S. Seo, D. G. Pintori, J. Finlayson, M. F. Greaney, Org. Lett. 2011, 13, 3667-3669
20. I.-K. Park, J. Park, C.-G. Cho, Angew. Chem. 2012, 124, 2546-2549
21. Angew. Chem. Int. Ed. 2012, 51, 2496-2499
22. S. Gore, S. Baskaran, B. König, Org. Lett. 2012, 14, 4568-4571.
23. S. A. Kozmin, T. Iwama, Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 4628-4641
24. G. Lawton, J. E. Saxton, A. J. Smith, Tetrahedron 1977, 33, 1641-1653, and references therein; for an example on regiochemistry of the Fischer indolization in synthetic study on Strychnos alkaloids, see
25. J. Bonjoch, N. Casamitjana, J. Quirante, M. Rodriguez, J. Bosch, J. Org. Chem. 1987, 52, 267-275.
26. H. Suzuki, A. Yamamoto, J. Chem. Res. Synop. 1992, 280-281
27. J. F. Hartwig, Angew. Chem. 1998, 110, 2249-2252
28. Angew. Chem. Int. Ed. 1998, 37, 2090-2092
29. A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727-7729
30. S. Cacchi, G. Fabrizi, A. Goggiamani, E. Licandro, S. Maiorana, D. Perdicchia, Org. Lett. 2005, 7, 1497-1500
31. J. Barluenga, P. Moriel, F. Aznar, C. Valdes, Org. Lett. 2007, 9, 275-278
32. L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem. 2009, 74, 4542-4546
33. A. Reichelt, J. R. Falsey, R. M. Rzasa, O. R. Thiel, M. M. Achmatowicz, R. D. Larsen, D. Zhang, Org. Lett. 2010, 12, 792-795
34. R. J. Lundgren, M. Stradiotto, Angew. Chem. 2010, 122, 8868-8872
35. Angew. Chem. Int. Ed. 2010, 49, 8686-8690
36. X. Xiong, Y. Jiang, D. Ma, Org. Lett. 2012, 14, 2552-2555
37. S. J. Welsch, C. Kalinski, M. Umkehrer, G. Ross, J. Kolb, C. Burdack, L. A. Wessjohann, Tetrahedron Lett. 2012, 53, 2298-2301; For other approaches to indoles employing hydrazines for hydroaminations, see
38. Y. Li, Y. Shi, A. L. Odom, J. Am. Chem. Soc. 2004, 126, 1794-1803
39. A. Tillack, H. Jiao, I. G. Castro, C. G. Hartung, M. Beller, Chem. Eur. J. 2004, 10, 2409-2420.
40. Y.-K. Lim, C.-G. Cho, Tetrahedron Lett. 2004, 45, 1857-1859.
41. S.-E. Suh, I.-K. Park, B.-Y. Lim, C.-G. Cho, Eur. J. Org. Chem. 2011, 455-457
42. H.-Y. Kim, W.-J. Lee, H.-M. Kang, C.-G. Cho, Org. Lett. 2007, 9, 3185-3186
43. H.-M. Kang, Y.-K. Lim, I.-J. Shin, H.-Y. Kim, C.-G. Cho, Org. Lett. 2006, 8, 2047-2050
44. Y.-K. Lim, K.-S. Lee, C.-G. Cho, Org. Lett. 2003, 5, 979-982.
45. A. Klapars, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 7421-7428
46. L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669.
47. 2 in the Fischer indole synthesis, see:, E. Fischer, Ber. Dtsch. Chem. Ges. 1886, 19, 1567.
48. L. K. Sydnes, K. F. S. Alnes, N. Erdogan, Monatsh. Chem. 2005, 136, 1737-1749.
49. H. Kim, S.-K. Lee, D. Lee, J. K. Cha, Synth. Commun. 1998, 28, 729-735.
50. D. L. Hughes, D. Zhao, J. Org. Chem. 1993, 58, 228-233.
51. P. L. Julian, J. Pikl, K. Boggess, J. Am. Chem. Soc. 1934, 56, 1797-1801
52. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1935, 57, 539-544.
53. F. E. King, R. Robinson, J. Chem. Soc. 1932, 326-336
54. B. K. Blount, R. Robinson, J. Chem. Soc. 1932, 1429-1433
55. F. E. King, R. Robinson, J. Chem. Soc. 1932, 1433-1438
56. F. E. King, R. Robinson, J. Chem. Soc. 1933, 270-273
57. F. E. King, M. Liguori, R. Robinson, J. Chem. Soc. 1934, 1416-1419.
58. I. I. Grandberg, T. I. Zuyanova, N. I. Afonina, T. A. Ivanova, Dokl. Akad. Nauk SSSR 1967, 176, 583-585
59. A. Z. Britten, W. G. Bardsley, C. M. Hill, Tetrahedron 1971, 27, 5631-5639
60. I. I. Grandberg, G. P. Tokmakov, Khim. Geterotsikl. Soedin. 1975, 207-210
61. P. Rosenmund, E. Sadri, Liebigs Ann. Chem. 1979, 927-943
62. P. Rosenmund, S. Gektidis, H. Brill, R. Kalbe, Tetrahedron Lett. 1989, 30, 61-62
63. S. Takano, M. Moriya, Y. Iwabuchi, K. Ogasawara, Chem. Lett. 1990, 109-112
64. R. Tsuji, M. Nakagawa, A. Nishida, Heterocycles 2002, 58, 587-593
65. B. W. Boal, A. W. Schammel, N. K. Garg, Org. Lett. 2003, 5, 3667-3669
66. A. Nishida, S. Ushigome, A. Sugimoto, S. Arai, Heterocycles 2005, 66, 181-185
67. A. W. Schammel, B. W. Boal, L. Zu, T. Mesganaw, N. K. Garg, Tetrahedron 2010, 66, 4687-4695
68. L. Zu, B. W. Boal, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 8877-8879
69. C. Bunders, J. Cavanagh, C. Melander, Org. Biomol. Chem. 2011, 9, 5476-5481
70. A. W. Schammel, G. Chiou, N. K. Garg, J. Org. Chem. 2012, 77, 725-728
71. A. W. Schammel, G. Chiou, N. K. Garg, Org. Lett. 2012, 14, 4556-4559.
72. J. Jobst, O. Hesse, Ann. Chem. Pharm. 1864, 129, 115-121
73. S. J. Traub, L. S. Nelson, R. S. Hoffman, J. Toxicol. Clin. Toxicol. 2002, 40, 781-787.
74. M. G. Kulkarni, A. P. Dhondge, A. S. Borhade, D. D. Gaikwad, S. W. Chavhan, Y. B. Shaikh, V. B. Ningdale, M. P. Desai, D. R. Birhade, M. P. Shinde, Tetrahedron Lett. 2009, 50, 2411-2413.
75. For the use of 1, 10-phenanthroline in copper-catalyzed coupling of hydrazides with aryl iodides, see:, M. Wolter, A. Klapars, S. L. Buchwald, Org. Lett. 2001, 3, 3803-3805.
76. G. Massiot, P. Thepenier, M. J. Jacquier, L. Le Men-Olivier, C. Delaude, Heterocycles 1989, 29, 1435-1438.
77. J. Mokrý, L. Dúbravková, P. Šefč ovič, Experientia 1962, 18, 564-565.
78. For a recent report on catalytic asymmetric Fischer indolization, see:, S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534-18537.