Intramolecular fischer indole synthesis and its combination with an aromatic [3,3]-sigmatropic rearrangement for the preparation of tricyclic benzo[cd]indoles

Angewandte Chemie - International Edition

Volumn 51, Issue 10, 2012, Pages 2496-2499

  Park, In Keol ^a   Park, Jun ^a   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

Author keywords

aryl hydrazides; benzo cd indoles; Fischer indole synthesis; polycycles; sigmatropic rearrangement

Indexed keywords

ARYL HYDRAZIDES; BENZO[CD]INDOLES; FISCHER INDOLE SYNTHESIS; POLYCYCLES; SIGMATROPIC REARRANGEMENTS;

AROMATIC COMPOUNDS; AROMATIZATION; TETHERLINES;

SYNTHESIS (CHEMICAL);

EID: 84863240749     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108970     Document Type: Article

References (53)

1. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875
2. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873
3. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045
4. J. E. Saxton, The Chemistry of Heterocyclic Compounds, Vol. 25, Part IV, Wiley, New York, 1983.
5. A. Rahman, Indole Alkaloids, Harwood Academic Publisher, Amsterdam, 1998
6. R. F. Raffauf, A Handbook of Alkaloids and Alkaloid-containing Plants, Wiley-Interscience, New York, 1970
7. A. Stoll, A. Hofman, in The Alkaloids Chemistry and Physiology, Vol. 8 (Ed.:, R. H. F. Manske,), Academic Press, New York, 1965, p. 725.
8. B. Robinson, The Fischer Indole Synthesis, Wiley, Chichester, 1982
9. D. L. Hugh, Org. Prep. Proced. Int. 1993, 25, 609; for catalytic asymmetric Fischer indolization, see
10. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534.
11. Y.-K. Lim, C.-G. Cho, Tetrahedron Lett. 2004, 45, 1857
12. J. Chae, S. L. Buchwald, J. Org. Chem. 2004, 69, 3336.
13. I.-K. Park, S.-E. Suh, B.-Y. Lim, C.-G. Cho, Org. Lett. 2009, 11, 5454.
14. L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem. 2009, 74, 4542
15. M. S. Lam, H. W. Lee, A. S. C. Chen, F. Y. Kwong, Tetrahedron Lett. 2008, 49, 6192
16. F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581
17. M. Wolter, A. Klapars, S. L. Buchwald, Org. Lett. 2001, 3, 3803
18. Z. Wang, R. T. Skerlj, G. J. Bridger, Tetrahedron Lett. 1999, 40, 3543.
19. For the Pd-catalyzed coupling reaction of hydrazine en route to aryl hydrazines, see:, R. J. Lundgren, M. Stradiotto, Angew. Chem. 2010, 122, 8868
20. Angew. Chem. Int. Ed. 2010, 49, 8686.
21. T. J. Greshock, R. L. Funk, J. Am. Chem. Soc. 2006, 128, 4946.
22. R. J. Rafferty, R. M. Williams, J. Org. Chem. 2012, 77, 519
23. X. Li, X. Gong, M. Zhao, G. Song, J. Deng, X. Li, Org. Lett. 2011, 13, 5808
24. D.-J. Cheng, H.-B. Wu, S.-K. Tian, Org. Lett. 2011, 13, 5636
25. K. S. Feldman, P. Ngernmeesri, Org. Lett. 2011, 13, 5704.
26. Z. Xu, Q. Li, L. Zhang, Y. Jia, J. Org. Chem. 2010, 75, 6316
27. J.-M. Ku, B.-S. Jeong, S.-S. Jew, H.-G. Park, J. Org. Chem. 2007, 72, 8115
28. Y. Yokoyama, H. Hikawa, M. Mitsuhashi, A. Uyama, Y. Hiroki, Y. Murakami, Eur. J. Org. Chem. 2004, 1244.
29. Z. Zuo, W. Xie, D. Ma, J. Am. Chem. Soc. 2010, 132, 13226
30. J. H. Seo, P. Liu, S. M. Weinreb, J. Org. Chem. 2010, 75, 2667
31. J. Yang, H. Wu, L. Shen, Y. Qin, J. Am. Chem. Soc. 2007, 129, 13794.
32. S. Inuki, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2011, 13, 2145
33. T. Kurokawa, M. Isomura, H. Tokuyama, T. Fukuyama, Synlett 2009, 775
34. S. K. Bur, A. Padwa, Org. Lett. 2002, 4, 4135
35. A. Liras, C. L. Lynch, A. M. Fryer, B. T. Vu, S. F. Martin, J. Am. Chem. Soc. 2001, 123, 5918.
36. A. D. Huters, K. W. Quasdorf, E. D. Styduhar, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 15797; for the synthesis of the welwitindolinone core or related compounds, see
37. V. Bhat, K. M. Allan, V. H. Rawal, J. Am. Chem. Soc. 2011, 133, 5798
38. V. Bhat, J. A. MacKay, V. H. Rawal, Org. Lett. 2011, 13, 3214
39. D. B. Freeman, A. A. Holubec, M. W. Weiss, J. A. Dixon, A. Kakefuda, M. Ohtsuka, M. Inoue, R. G. Vaswani, H. Ohki, B. D. Doan, S. E. Reisman, B. M. Stoltz, J. J. Day, R. N. Tao, N. A. Dieterich, J. Wood, Tetrahedron 2010, 66, 6647
40. J. A. Brailsford, R. Lauchli, K. J. Shea, Org. Lett. 2009, 11, 5330
41. T. J. Greshock, R. L. Funk, Org. Lett. 2006, 8, 2643.
42. S.-E. Suh, I.-K. Park, B.-Y. Lim, C.-G. Cho, Eur. J. Org. Chem. 2011, 455
43. W.-J. Lee, H.-Y. Kim, C.-G. Cho, Org. Lett. 2007, 9, 3185
44. H.-Y. Kim, W.-J. Lee, H.-M. Kang, C.-G. Cho, Bull. Korean Chem. Soc. 2007, 28, 1821
45. H.-M. Kang, H.-Y. Kim, J.-W. Jung, C.-G. Cho, J. Org. Chem. 2007, 72, 679
46. H.-M. Kang, Y.-K. Lim, I.-J. Shin, H.-Y. Kim, C.-G. Cho, Org. Lett. 2006, 8, 2047
47. Y.-K. Lim, J.-W. Jung, C.-G. Cho, J. Org. Chem. 2004, 69, 5778
48. Y.-K. Lim, S. Choi, K. B. Park, C.-G. Cho, J. Org. Chem. 2004, 69, 2603
49. K.-S. Lee, K.-Y. Kim, J.-T. Shin, C.-G. Cho, Tetrahedron Lett. 2004, 45, 117
50. Y.-K. Lim, S.-J. Pang, S.-U. Paek, H. Lee, C.-G. Cho, Bull. Korean Chem. Soc. 2003, 24, 543
51. Y.-K. Lim, K.-S. Lee, C.-G. Cho, Org. Lett. 2003, 5, 979
52. G.-S. Lee, Y.-K. Lim, C.-G. Cho, Tetrahedron Lett. 2002, 43, 7463.
53. N. Çelebi-Ölçüm, B. W. Boal, A. D. Huters, N. K. Garg, K. N. Houk, J. Am. Chem. Soc. 2011, 133, 5752.