Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles

Organic Letters

Volumn 8, Issue 18, 2006, Pages 4093-4096

  Ballini, Roberte ^a   Palmieri, Alessandro ^a   Petrini, Marino ^a   Torregiani, Elisabetta ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM SILICATE; INDOLE DERIVATIVE; SULFONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CLAY;

ALUMINUM SILICATES; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; SULFONES;

EID: 33748948395     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061604w     Document Type: Article

References (50)

1. (a) Faulkner, D. J. Nat. Prod. Rep. 2002, 1-48.
2. (b) Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998.
3. (c) Sundberg, R. J. Indoles; Academic Press: New York, 1997.
4. (d) Saxton, J. E. Nat. Prod. Rep. 1997, 559-590.
5. (a) Ballini, R.; Rabanedo Clemente, R.; Palmieri, A.; Petrini, M. Adv. Synth. Catal. 2006, 348, 191-196.
6. (b) Wynne, J. H.; Stalick, W. M. J. Org. Chem. 2002, 67, 5850-5853.
7. (c) Mahboobi, S.; Wiegrebe, W.; Popp, A. J. Nat. Prod. 1999, 62, 577-579.
8. (d) Koike, T.; Takeuchi, N.; Hagiwara, M.; Yamazaki, K.; Tobinaga, S. Heterocycles 1999, 51, 2687-2695.
9. (e) Koike, T.; Hagiwara, M.; Takeuchi, N.; Tobinaga, S. Heterocycles 1997, 45, 1271-1280.
10. Review: (a) Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199-1222.
11. For some very recent examples see: (b) Jia, Y.-X.; Zhu, S. F.; Yang, Y.; Zhou, Q.-L. J. Org. Chem. 2006, 71, 75-80.
12. (c) Yamazaki, S.; Iwata, Y. J. Org. Chem. 2006, 71, 739-743.
13. (d) Lu, S.-F.; Du, D.-M.; Xu, J. Org. Lett. 2006, 8, 2115-2118.
14. (e) Li, D.-P.; Guo, Y.-C.; Ding, Y.; Xiao, W.-J. Chem. Commun. 2006, 799-801.
15. (f) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942-8943.
16. (g) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576-6579.
17. (h) Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154-4155.
18. Acid catalysis can be sometimes avoided when particularly reactive electrophiles are used in the reaction with indoles: (a) Jiang, B.; Huang, Z.-G. Synthesis 2005, 2198-2204.
19. (b) Dessole, G.; Herrera, R. P.; Ricci, A. Synlett 2004, 2374-2378.
20. (a) Mi, X.; Luo, S.; He, J.; Cheng, J.-P. Tetrahedron Lett. 2004, 45, 4567-4570.
21. (b) Xie, W.; Bloomfield, K. M.; Jin, Y.; Dolney, N.; Wang, P. G. Synlett 1999, 498-500.
22. (a) Semenov, B. B.; Novikov, K. A.; Lysenko, K. A.; Kachala, V. V. Tetrahedron Lett. 2006, 47, 3479-3483.
23. (b) Freed, J. D.; Hart, D. J.; Magomedov, N. A. J. Org. Chem. 2001, 66, 839-852.
24. (c) Dubois, L.; Dorey, G.; Potier, P.; Dodd, R. H. Tetrahedron: Asymmetry 1995, 6, 455-462.
25. (a) Fišera, L. Science of Synthesis; Padwa, A., Ed.; Thieme: Stuttgart, 2004; Vol. 27, p 349.
26. (b) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
27. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856.
28. (a) Wang, Y.-Q.; Song, W. J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156-8157.
29. (b) Jia, Y.-X.; Xie, J.-H.; Duan, H.-F.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2006, 8, 1621-1624.
30. (c) Johannsen, M. Chem. Commun. 1999, 2233-2234.
31. DeNinno, M. P.; Eller, C.; Etienne, J. B. J. Org. Chem. 2001, 66, 6988-6993.
32. (a) Singh, D. U.; Singh, P. R.; Samant, S. D. Synth. Commun. 2006, 36, 1265-1271.
33. (b) Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2005, 70, 1941-1944.
34. (c) Bandini, M.; Fagioli, M.; Umani-Ronchi, A. Adv. Synth. Catal. 2004, 346, 545-548.
35. (d) Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 68, 4594-4597.
36. (e) Chakrabarty, M.; Basak, R.; Ghosh, N. Tetrahedron Lett. 2001, 42, 3913-3915
37. (a) Petrini, M. Chem. Rev. 2005, 105, 3949-3977.
38. (b) Petrini, M.; Torregiani, E. Tetrahedron Lett. 2005, 46, 5999-6003.
39. Extensive decomposition of the α-amido sulfone has been observed in this process, especially for tert-butyloxycarbamoyl sulfones.
40. Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751-1753.
41. Under certain circumstances, the bisindole is stable enough with respect to the sulfonyl indole that it may become the main product as in the reaction of indole 1b with imino ester precursor 6f that gives predominantly bisindole 15. (Diagram Presented)
42. (a) Nâjera, C.; Yus, M. Tetrahedron 1999, 55, 10547-10658.
43. (b) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon Press: Oxford, 1993.
44. (a) Padwa, A.; Muller, C. L.; Rodriguez, A.; Watterson, S. H. Tetrahedron 1998, 55, 9651-9666.
45. (b) Morimoto, Y.; Mikami, A.; Kuwabe, S.; Shirahama, H. Tetrahedron: Asymmetry 1996, 7, 3371-3390.
46. (c) Giovannini, R.; Petrini, M. Synlett 1995, 973-974.
47. (d) Smith, A. B., III; Hale, K. J.; McCauley, J. P., Jr. Tetrahedron Lett. 1989, 30, 5579-5582.
48. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1345-1353.
49. (a) Krasovsky, A. L.; Druzhinin, S. V.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron Lett. 2004, 45, 1129-1132.
50. (b) Licari, J. J.; Dougherty, G. J. Am. Chem. Soc. 1954, 76, 4039-4040.