Reaction of 3-(1-arylsulfonylalkyl)-indoles with easily enolisable derivatives promoted by potassium fluoride on basic alumina

Advanced Synthesis and Catalysis

Volumn 350, Issue 1, 2008, Pages 129-134

  Ballini, Roberto ^a   Palmieri, Alessandro ^a   Petrini, Marino ^a   Shaikh, Rafik R ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Basic alumina; Carbanions; Conjugate addition; Heterogeneous catalysis; Indoles

Indexed keywords

EID: 38349147664     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700410     Document Type: Article

References (62)

1. a) D. J. Faulkner, Nat. Prod. Rep. 2002, 1-48;
2. b) J. E. Saxton, in: The Alkaloids, (Ed.: G.A. Cordell), Academic Press, New York, 1998;
3. c) R. J. Sundberg, Indoles, Academic Press, New York, 1997;
4. d) J. E. Saxton, Nat. Prod. Rep. 1997, 559-590.
5. M. Bandini, A. Melloni, S. Tommasi, A. UmaniRonchi, Synlett 2005, 1199-1222.
6. a) B. B. Semenov, V. G. Granik, Pharm. Chem. J. 2004, 38, 287-310; for some recent applications of gramines in synthesis:
7. b) G. de La Herrán, A. Segura, A. G. Csáky, Org. Lett. 2007, 9, 961-964;
8. c) B. B. Semenov, K. A. Novikov, K. A. Lysenko, V. V. Kachala, Tetrahedron Lett. 2006, 47, 3479-3483;
9. d) K. H. Low, N. A. Magomedov, Org. Lett. 2005, 7, 2003-2005.
10. a) M. Iwao, O. Motoi, Tetrahedron Lett. 1995, 36, 5929-5932;
11. b) G. D. H. Dijkstra, M. T. M. Tulp, P. H. H. Hermkens, J. H. van Maarseveen, H. W Scheeren, C. G. Kruse, Ree Trav. Chim. Pays-Bas 1993, 112, 131-136;
12. c) P. H. H. Hermkens, J. H. van Maarseveen, H.C.J. Ottenheijm, C.G. Kruse, H.W. Scheeren, J. Org. Chem. 1990, 55, 3998-4006;
13. d) P. H. H. Hermkens, van J. H. Maarseveen, P. L. H. M. Cobben, H. C. J. Ottenheijm, C. G. Kruse, H. W Scheeren, Tetrahedron 1990, 46, 833-846.
14. a) Y. Gong, K. Kato, H. Kimoto, Tetrahedron Lett. 1999, 40, 5743-5744;
15. b) D. R. Witty, G. Walker, J. H. Bateson, P. J. O'Hanlon, R. Cassels, Bioorg. Med. Chem. Lett. 1996, 6, 1375-1380.
16. a) H.-M. Dong, H.-H. Lu, L.-Q. Lu, C.-B. Chen, W.-J. Xiao, Adv. Synth. Cat. 2007, 349, 1597-1603;
17. b) H. Hagiwara, M. Sekifuji, T. Hoshi, K. Qiao, C. Yokoyama, Synlett 2007, 1320-1322;
18. c) H. M. Kaiser, W.F. Lo, A. M. Riahi, A. Spannenberg, M. Beller, M. K. Tse, Org. Lett. 2006, 8, 5761-5764;
19. d) G. Cravotto, G.B. Giovenzana, A. Maspero, T. Pilati, A. Penoni, G. Palmisano, Tetrahedron Lett. 2006, 47, 6439-6443;
20. e) P. K. Pradham, D. Dey, V. S. Giri, P. Jaisankar, Synthesis 2005, 1779-1782;
21. f) S. Kumar, V. Kumar, S. S. Chimmi, Tetrahedron Lett. 2003, 44, 2101-2104.
22. a) C. Nájera, M. Yus, Tetrahedron 1999, 55, 10547-10658;
23. b) N S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993.
24. a) J. J. Licari, G. Dougherty, J. Am. Chem. Soc. 1954, 76, 4039-4040; for the synthesis of a particular 3-(1,2-bisarylsulfonyl- 2-trifluorocarbonyl)-indole see:
25. b) A. L. Krasovsky, S. V Druzhinin, V. G. Nenajdenko, E. S. Balenkova, Tetrahedron Lett. 2004, 45, 1129-1132.
26. M. Petrini, Chem. Rev. 2005, 105, 3949-3977.
27. 3-catalysed reaction of a-amido sulfones with electron-rich aromatics see:
28. b) C. Kuhakarn, K. Tangdenpaisal, P. Kongsaeree, S. Prabpai, P. Tuchinda, M. Pohmakotr, V. Reutrakul, Tetrahedron Lett. 2007, 48, 2467-2470.
29. A. Palmieri, M. Petrini, J. Org. Chem. 2007, 72, 1863-1866.
30. a) N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001;
31. b) R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, M. Petrini, Chem. Rev. 2005, 105, 933-971;
32. c) F. A. Luzzio, Tetrahedron 2001, 57, 915-945.
33. a) R. Ballini, M. Petrini Tetrahedron 2004, 60, 10171047;
34. b) N. Ono, H. Miyake, R. Tamura, A. Kaji, Tetrahedron Lett.1981, 22, 1705-1708;
35. c) T. C. Fessard, H. Motoyoshi, E. M. Carreira, Angew. Chem. 2007, 119, 2124-2127;
36. Angew. Chem. Int. Ed. 2007, 46, 2078-2081.
37. A. Palmieri, M. Petrini, E. Torregiani, Tetrahedron Lett. 2007, 48, 5653-5656.
38. a) G. W. Kabalka, R. M. Pagni, Tetrahedron 1997, 53, 7999-8065; for some recent applications of KF-basic alumina see:
39. b) Y. Ge, L. Hu, Tetrahedron Lett. 2007, 48, 4585-4588;
40. c) M. Boruah, D. Konwar, S.D. Sharma, Tetrahedron Lett. 2007, 48, 4535-4537;
41. d) R. Ballini, A. Palmieri, Adv. Synth. Cat. 2006, 348, 1154-1156;
42. e) R. Ballini, R. R. Clemente, A. Palmieri, M. Petrini, Adv. Synth. Cat. 2006,348, 191-196.
43. Reaction of nitroalkanes with gramines occurs at reflux under various conditions: a) K. Miyashita, K. Kondoh, K. Tsuchiya, H. Miyabe, T. Imanishi, Chem. Pharm. Bull. 1997, 45, 932-935;
44. b) M. W. Maichrzak, J.N. Zobel, D. J. Obradovich, Synth. Commun. 1997, 27, 3201-3211;
45. c) Y Endo, T. Imada, K. Yamaguchi, K. Shudo, Heterocycles 1994, 39, 571-579;
46. d) A. M. Thompson, D. W Fry, A. J. Kraker, W A. Denny, J. Med. Chem. 1994, 37, 598-609;
47. e) J. Quick, B. Saha, P. E. Driedger, Tetrahedron Lett. 1994, 35, 8549-8552;
48. f) M. Li, M. E. Johnson, Tetrahedron Lett. 1994, 35, 6255-6258.
49. W E. Kreighbaum, W. L. Matier, R. D. Dennis, J. L. Minielli, D. Deitchman, J. L. Perlach, W. T. Comer, J. Med. Chem. 1980, 23, 285-289.
50. a) R. Cao, W. Peng, Z. Wang, A. Xu, Curr. Med. Chem. 2007, 14, 479-500;
51. b) Z. Czarnocki, A. Siwicka, J. Szawkalo, Curr. Org. Synth. 2005, 2, 301-331;
52. c) L. Jeannin, M. Boisbrun, C. Nemes, F. Cochard, M. Laronze, E. Dardennes, Á. Kovács-Kulyassa, J. Sapi, J.-Y. Laronze, C. R. Chimie 2003, 6, 517-528.
53. a) L. Jeannin, T. Nagy, E. Vassileva, J. Sapi, J.-Y. Laronze, Tetrahedron Lett. 1995, 36, 2057-2058;
54. b) C. Nemes, L. Jeannin, J. Sapi, M. Laronze, H. Seghir, F. Auge, J.-Y. Laronze, Tetrahedron 2000, 56, 5479-5492.
55. a) D. T. Jones, G. T. Hartman III, R. M. Williams, Tetrahedron Lett. 2007, 48, 1291-1294;
56. b) X. Teng, A. Degterev, P. Jagtap, X. Xing, S. Choi, R. Denu, J. Yuan, G. D. Cuny, Bioorg. Med. Chem. Lett. 2005, 15, 5039-5044;
57. c) R. M. Williams, J. Cao, H. Tsujishima, R.J. Cox, J. Am. Chem. Soc. 2003, 125, 12172-12178;
58. d) V. Marcq, C. Mirand, M. Decarme, H. Emonard, W. Hornebeck, Bioorg. Med. Chem. Lett. 2003, 13, 2843-2846;
59. e) B. Meseguer, D. Alonso-Díaz, N. Griebenov, T. Herget, H. Waldmann, Chem. Eur. J. 2000, 6, 3943-3957.
60. A. K. Sinhababu, R. T. Borchardt, Tetrahedron Lett. 1983, 24, 227-230.
61. R. Ballini, M. Petrini, Synth. Commun. 1986, 16, 1781 -1788.
62. D. E. Bergbreiter, J. J. Lalonde, J. Org. Chem. 1987, 52, 1601-1603.