Concise synthesis of indole-fused 1,4-diazepines through copper(l)-catalyzed domino three-component coupling-cyclization-N-arylation under microwave irradiation

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3535-3538

  Ohta, Yusuke ^a   Chiba, Hiroaki ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a   Ohno, Hiroaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ANILINE DERIVATIVE; AZEPINE DERIVATIVE; COPPER; DRUG DERIVATIVE; INDOLE; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; RADIATION EXPOSURE; STEREOISOMERISM; SYNTHESIS;

ACETYLENE; ANILINE COMPOUNDS; AZEPINES; CATALYSIS; COPPER; CYCLIZATION; INDOLES; MICROWAVES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 54049091217     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801383b     Document Type: Article

References (37)

1. For a recent review on concurrent tandem catalysis, see: (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020. See also:
2. (b) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186.
3. For representative examples, see: (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848.
4. (b) Jeong, N.; Seo, S. D.; Shin, J. Y. J. Am. Chem. Soc. 2000, 122, 10220-10221.
5. (c) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872-12873.
6. (d) Son, S. U.; Park, K. H.; Seo, H.; Chung, Y. K.; Lee, S.-G. Chem. Commun. 2001, 2440-2441.
7. (e) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390-13391.
8. (f) Komon, Z. J. A.; Diamond, G. M.; Leclerc, M. K.; Murphy, V.; Okazaki, M.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 15280-15285.
9. (g) Dijk, E. W.; Panella, L.; Pinho, P.; Naasz, R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2004, 60, 9687-9693.
10. (h) van As, B. A. C.; van Buijtenen, J.; Heise, A.; Broxterman, Q. B.; Verzijl, G. K. M.; Palmans, A. R. A.; Meijer, E. W. J. Am. Chem. Soc. 2005, 127, 9964-9965.
11. For reviews, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
12. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
13. (c) Chemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153-1160.
14. (d) Carril, M.; SanMartin, R.; Domínguez, E. Chem. Soc. Rev. 2008, 37, 639-647.
15. For selected examples of tandem catalytic reaction using a copper salt including two catalytic cycles, see: (a) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280.
16. (b) Kamijo, S.; Sasaki, Y.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 35-38.
17. (c) Li, K.; Alexakis, A. Tetrahedron Lett. 2005, 46, 8019-8022.
18. (d) Loones, K. T. J.; Maes, B. U. W.; Meyers, C.; Deruytter, J. J. Org. Chem. 2006, 71, 260-264.
19. (e) Yuen, J.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 653-656.
20. (f) Zhang, L.; Malinakova, H. C. J. Org. Chem. 2007, 72, 1484-1487.
21. (g) Martin, R.; Laursen, C. H.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 3379-3382.
22. (h) Français, A.; Urban, D.; Beau, J.-M. Angew. Chem., Int. Ed. 2007, 46, 8662-8665.
23. (i) Kumaraswamy, G.; Ankamma, K.; Pitchaiah, A. J. Org. Chem. 2007, 72, 9822-9825.
24. (a) Maryanoff, B. E.; Nortey, S. O.; Gardocki, J. F. J. Med. Chem. 1984, 27, 1067-1071.
25. (b) Ho, C. Y.; Hageman, W. E.; Persico, F. J. J. Med. Chem. 1986, 29, 1118-1121.
26. (c) Suzuki, H.; Shinpo, K.; Yamazaki, T.; Niwa, S.; Yokoyama, Y.; Murakami, Y. Heterocycles 1996, 42, 83-86.
27. (d) Sasaki, S.; Ehara, T.; Sakata, I.; Fujino, Y.; Harada, N.; Kimura, J.; Nakamura, H.; Maeda, M. Bioorg. Med. Chem. Lett. 2001, 11, 583-585.
28. (e) Kau, T. R.; Schroeder, F.; Ramaswaray, S.; Wojciechowski, C. L.; Zhao, J. J.; Roberts, T. M.; Clardy, J.; Sellers, W. R.; Silver, P. A. Cancer Cell 2003, 4, 463-476.
29. (f) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Olson, R. M.; Knauer, C. S.; Chio, C. L.; Hyslop, D. K.; Campbell, J. E.; Fitzgerald, L. W.; Nichols, N. F.; Svensson, K. A.; McCall, R. B.; Haber, C. L.; Kagey, M. L.; Dinh, D. M. Bioorg. Med. Chem. Lett. 2003, 13, 2369-2372.
30. (g) Ducker, C. E.; Griffel, L. K.; Smith, R. A.; Keller, S. N.; Zhuang, Y.; Xia, Z.; Diller, J. D.; Smith, C. D. Mol. Cancer Ther. 2006, 5, 1647-1659.
31. (h) Yang, S.-M.; Malaviya, R.; Wilson, L. J.; Argentieri, R.; Chen, X.; Yang, C.; Wang, B.; Cavender, D.; Murray, W. V. Bioorg. Med. Chem. Lett. 2007, 17, 326-331.
32. Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew. Chem., Int. Ed. 2007, 46, 2295-2298.
33. For a related isoquinoline formation, see: (a) Ohta, Y.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun. 2008, 835-837.
34. One portion addition of all the reactants including the alkoxide at the beginning of the reaction caused decomposition of the starting material.
35. For patent information including a related tetracyclic compound, see: Ivashchenko, A. V.; Ilyin, A. P.; Kysil, V. M.; Trifilenkov, A. S.; Tsirulnikov, S. A.; Shkirando, A. M.; Churakova, M. V.; Lomakina, I. O.; Potapov, V. V.; Zamaletdinova, A. I.; Tkachenko, S. Y.; Kravchenko, D. V.; Khvat, A. V.; Okun, I. M.; Kyselev, A. S. PCT Int. Appl. 2007, WO2007117180.
36. Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
37. Since the formation 2-(aminomethyl)indole using 1b and 2d proceeded efficiently (quantitative yield), deprotection conditions using MeONa caused undesired side reactions.