3-Aroylindoles via copper-catalyzed cyclization of N-(2-iodoaryl)enaminones

Synlett

Volumn , Issue 9, 2009, Pages 1480-1484

  Bernini, Roberta ^a   Cacchi, Sandro ^b   Fabrizi, Giancarlo ^b   Filisti, Eleonora ^b   Sferrazza, Alessio ^a  

^a UNIVERSITY OF TUSCIA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Catalysis; Copper; Cyclization; Enaminones; Indoles

Indexed keywords

ANILINE DERIVATIVE; COPPER; ETHER; INDOLE DERIVATIVE; IODINE DERIVATIVE; KETONE;

ARTICLE; CATALYST; CYCLIZATION; PROCESS OPTIMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 67649397429     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216742     Document Type: Article

References (48)

1. Wijsmuller, W. F. A.; Wanner, M. J.; Koomen, G.-J.; Pandit, U. K. Heterocycles 1986, 24, 1795.
2. (a) Bell, M. R.; D'Ambra, T. E.; Kumar, V.; Eissenstat, M. A.; Herrmann, J. L. Jr.; Wetzel, J. R.; Rosi, D.; Philion, R. E.; Daum, S. J.; Hlasta, D. J.; Kullnig, R. K.; Ackerman, J. H.; Haubrich, D. R.; Luttinger, D. A.; Baizman, E. R.; Miller, M. S.; Ward, S. J. J. Med. Chem. 1991, 34, 1099.
3. (b) D'Ambra, T. E.; Estep, K. G.; Bell, M. R.; Eissenstat, M. A.; Josef, K. A.; Ward, S. J.; Haycock, D. A.; Baizman, E. R.; Casiano, F. M.; Beglin, N. C.; Chippari, S. M.; Grego, J. D.; Kullnig, R. K.; Daley, G. T. J. Med. Chem. 1992, 35, 124.
4. (c) Sheppard, G. S.; Pireh, D.; Carrera, G. M.; Bures, M. G.; Heyman, H. R.; Steinman, D. H.; Davidsen, S. K.; Phillips, J. G.; Guinn, D. E.; May, P. D.; Conway, R. D.; Rhein, D. A.; Calhoun, W. C.; Albert, D. H.; Magoc, T. J.; Carter, G. W.; Summers, J. B. J. Med. Chem. 1994, 37, 2011.
5. (d) Lehr, M. J. Med. Chem. 1997, 40, 2694.
6. (e) Curtin, M. L.; Davidsen, S. K.; Heyman, H. R.; Garland, R. B.; Sheppard, G. S.; Florjancic, A. S.; Xu, L.; Carrera, G. M.; Steinman, D. H.; Trautmann, J. A.; Albert, D. H.; Magoc, T. J.; Tapang, P.; Rhein, D. A.; Conway, R. G.; Luo, G.; Denissen, J. F.; Marsh, K. C.; Morgan, D. W.; Summers, J. B. J. Med. Chem. 1998, 41, 74.
7. For the acylation of N-protected indoles, see: (a) Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451.
8. For the acylation of NH free indoles, see: (b) Ottoni, O.; Neder, A. de.V.F.; Dias, A. K. D.; Cruz, R. P. A.; Equino, L. B. Org. Lett. 2001, 7, 1005.
9. For the preparation of 3-acylindoles via the Vilsmeier-Haack reaction, see: (c) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
10. For the acylation of indole Grignard reagents, see: (d) Heacock, R. A.; Kasparek, S. Adv. Heterocycl. Chem. 1969, 10, 61. see ref. 3c.
11. For the acylation of 3-indolylzinc chlorides, see: (e) Bergman, J.; Venemalm, L. Tetrahedron 1990, 46, 6061.
12. (f) Faul, M. M.; Winneroski, L. L. Tetrahedron Lett. 1997, 38, 4749.
13. For other procedures, see: (g) Bergman, J.; Bäckvall, J. E.; Lindströn, J. O. Tetrahedron 1973, 29, 971.
14. (h) Eyley, S. C.; Giles, R. G.; Heaney, H. Tetrahedron Lett. 1985, 26, 4649.
15. (i) Pindur, U.; Flo, C.; Akgun, E.; Tunali, M. Liebigs Ann. Chem. 1986, 9, 1621.
16. (j) Pfeuffer, L.; Sody, E.; Pindur, U. Chem.-Ztg. 1987, 111, 84.
17. (a) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215.
18. (b) Arcadi, A.; Cacchi, S.; Carnicellli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
19. Osuka, A.; Mori, Y.; Suzuki, H. Chem. Lett. 1982, 2031.
20. For recent reviews, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem. 2003, 115, 5558.
21. (b) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
22. (c) Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev. 2008, 108, 2916.
23. (d) Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359.
24. (e) Alexakis, A.; Backvall, J. E.; Krause, N.; Pamies, O.; Dieguez, M. Chem. Rev. 2008, 108, 2796.
25. (f) Yamada, K.-i.; Tomioka, K. Chem. Rev. 2008, 108, 2874.
26. (g) Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887.
27. (h) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853.
28. (i) Carril, M.; SanMartin, R.; Dominguez, E. Chem. Soc. Rev. 2008, 37, 639.
29. Cacchi, S.; Fab rizi, G. Chem. Rev. 2005, 105, 2873.
30. Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
31. (a) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008, 10, 2629.
32. (b) Bernini, R.; Cacchi, S.; Fabrizi, G.; Sferrazza, A. Synthesis 2009, 1209.
33. Karpov, A. S.; Müller, T. J. Org. Lett. 2003, 5, 3451.
34. 2: C, 76.51; H, 4.67. Found: C, 76.40; H, 4.58.
35. Compounds 2a and 3 were isolated in 30% and 60% yield, respectively, when the reaction was carried out in DMA at 120°C (3 h).
36. 15NO:C, 84.82; H, 5.08. Found: C, 84.71; H, 5.19.
37. Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708.
38. (a) Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133.
39. (b) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
40. For some recent leading references on the copper-catalyzed construction of the indole ring, see: (a) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
41. (b) Lu, B.; Ma, D. Org. Lett. 2006, 8, 6115.
42. (c) Yuen, J.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 653.
43. (d) Chen, Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329.
44. (e) Tanimori, S.; Ura, H.; Kirihata, M. Eur. J. Org. Chem. 2007, 3977.
45. (f) Hiroaki, O.; Yusuke, O.; Shinya, O.; Nobutaka, F. Angew. Chem. Int. Ed. 2007, 46, 2295.
46. (g) Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett. 2008, 10, 625.
47. For some recent leading references on the copper-catalyzed functionalization of indole rings, see: (a) Coste, A.; Toumi, M.; Wright, K.; Razafimahaléo, V.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 3841.
48. (b) Toumi, M.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 5027.