Regioselective C 2 sulfonylation of indoles mediated by molecular iodine

Journal of Organic Chemistry

Volumn 79, Issue 4, 2014, Pages 1778-1785

  Katrun, Praewpan ^a   Mueangkaew, Charoensak ^a   Pohmakotr, Manat ^a   Reutrakul, Vichai ^a   Jaipetch, Thaworn ^b   Soorukram, Darunee ^a   Kuhakarn, Chutima ^a  

^a Mahidol University ^*  (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; IODINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

INDOLES; IODINE; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 84894576414     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402831k     Document Type: Article

References (59)

1. Ban, Y.; Murakami, Y.; Iwasawa, Y.; Tsuchiya, M.; Takano, N. Med. Res. Rev. 1988, 8, 231
2. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 2000.
3. Seigler, D. S. Plant Secondary Metabolism; Springer: New York, 2001; pp 628-667.
4. Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148
5. Takayama, H.; Tsutsumi, S. I.; Kitajima, M.; Santiarworn, D.; Liawruangrath, B.; Aimi, N. Chem. Pharm. Bull. 2003, 51, 232
6. Humphrey, G. R.; Tsutumi, J. T. Chem. Rev. 2006, 106, 2875
7. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
8. Bentley, J. M.; Bickerdike, M. J.; Hebeisen, P.; Kennett, G. A.; Lightowler, S.; Mattei, P.; Mizrahi, J.; Morley, T. J.; Plancher, J.-M.; Richter, H. WO20020704, 2002.
9. Campbell, J. A.; Bordunov, V.; Borka, C. A.; Browner, M. F.; Kress, J. M.; Mirzadegan, T.; Ramesha, C.; Sanpablo, B. F.; Stabler, R.; Takahara, P.; Villasenor, A.; Walker, K. A. M.; Wang, J.-H.; Welch, M.; Weller, P. Bioorg. Med. Chem. Lett. 2004, 14, 4741
10. Holenz, J.; Pauwels, P. J.; Diaz, J. L.; Mercè, R.; Codony, X.; Buschmann, H. Drug Discovery Today 2006, 11, 283
11. Tong, L.; Shankar, B. B.; Chen, L.; Rizvi, R.; Kelly, J.; Gilbert, E.; Huang, C.; Yang, D.-Y.; Kozlowski, J. A.; Shih, N.-Y.; Gonsiorek, W.; Hipkin, R. W.; Malikzay, A.; Lunn, C. A.; Lundell, D. J. Bioorg. Med. Chem. Lett. 2010, 20, 6785
12. Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani, S. K.; Condra, J. H.; Emini, E. A.; Goldman, M. E.; Greenlee, W. J.; Kauffman, L. R.; O'Brien, J. A.; Sardana, V. V.; Schleif, W. A.; Theoharides, A. D.; Anderson, P. S. J. Med. Chem. 1993, 36, 1291
13. Romey, G.; Lazdunski, M. J. Pharmacol. Exp. Ther. 1994, 271, 1348
14. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Bird, C. W., Eds.; Pergamon Press: Oxford, UK, 1996; Vol. 2, pp 119-206.
15. Sundberg, R. J. Indoles; Academic Press: London, 1996.
16. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Bird, C. W., Eds.; Pergamon Press: Oxford, UK, 1996; Vol. 2, pp 207-257.
17. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
18. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195
19. Ackermann, L.; Dell'Acqua, M.; Fenner, S.; Vicente, R.; Sandmann, R. Org. Lett. 2011, 13, 2358
20. England, D. B.; Padwa, A. Org. Lett. 2008, 10, 3631
21. Liu, K.; Wen, P.; Liu, J.; Huang, G. Synthesis 2010, 3623
22. Choy, P. Y.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2011, 76, 80
23. Lubriks, D.; Sokolovs, I.; Suna, E. Org. Lett. 2011, 13, 4324
24. Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436
25. Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11689
26. Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066
27. Simpkins, N. S. In Sulfones in Organic Synthesis; Baldwin, J. E., Ed.; Pergamon Press: Oxford, UK, 1993.
28. Trost, B. M. In Comprehensive Organic Chemistry; Pergamon Press: Oxford, UK, 1991.
29. Asai, T.; Takeuchi, T.; Diffenderfer, J.; Sibley, D. L. Antimicrob. Agents Ch. 2002, 46, 2393
30. Caddick, S.; Aboutayab, K.; West, R. Synlett 1993, 231
31. Hamel, P.; Girard, Y.; Atkinson, J. G. J. Org. Chem. 1992, 57, 2694
32. Katritzky, A. R.; Lue, P.; Chen, Y.-X. J. Org. Chem. 1990, 55, 3688
33. Caddick, S.; Shering, C. L.; Wadman, S. N. Tetrahedron 2000, 56, 465
34. Stella, N.; Kline, T. Preparation of Naphthoylindole Derivatives for Treating Glioblastoma. Int. Appl. WO 2012024670, February 23, 2012.
35. Tocco, G.; Begala, M.; Esposito, F.; Caboni, P.; Cannas, V.; Tramontano, E. Tetrahedron Lett. 2013, 54, 6237
36. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702
37. Boroujeni, K. P. Bull. Korean Chem. Soc. 2010, 31, 1887
38. Boroujeni, K. P. J. Sulfur Chem. 2010, 31, 197
39. Yadav, J. S.; Reddy, B. V. V; Krishna, A. D.; Swamy, T. Tetrahedron Lett. 2003, 44, 6055
40. Liu, X.-Y.; Gao, P.; Shen, Y.-W.; Liang, Y.-M. Org. Lett. 2011, 13, 4196
41. Li, Y.-X.; Wang, H.-X.; Ali, S.; Xia, X.-F.; Liang, Y.-M. Chem. Commun. 2012, 48, 2343
42. Xiao, F.; Chen, H.; Xie, H.; Chen, S.; Yang, L.; Deng, G.-J. Org. Lett. 2014, 16, 50
43. da Silva Correîa, C. M. M.; Waters, W. A. J. Chem. Soc. C 1968, 1874
44. Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727
45. Truce, W. E.; Heuring, D. L.; Wolf, G. C. J. Org. Chem. 1974, 39, 238
46. Liu, L. K.; Chi, Y.; Jen, K.-Y. J. Org. Chem. 1980, 45, 406
47. Harwood, L. M.; Julia, M.; Thuillier, G. L. Tetrahedron 1980, 36, 2483
48. Barluenga, J.; Martínez-Gallo, J. M.; Nájera, C.; Yus, M.; Fananas, F. J. J. Chem. Soc., Perkin Trans. 1 1987, 2605
49. Nájera, C.; Baldó, B.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1988, 1029
50. da Silva Correîa, C. M. M.; Fleming, M. D. C. M.; Oliveira, M. A. B. C. S. J. Chem. Soc., Perkin Trans. 2 1994, 1993
51. Nájera, C.; Sansano, J. M.; Yus, M. J. Chem. Educ. 1995, 72, 664
52. Craig, D. C.; Edwards, G. L.; Muldoon, C. A. Synlett 1997, 1441
53. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 113, 4702
54. Karchava, A. V.; Shuleva, I. S.; Ovcharenko, A. A.; Yurovskaya, M. A. Khim. Geterotsikl. Soedin. 2010, 373
55. Chem. Heterocycl. Compd. 2010, 46, 291.
56. Pfister, J. R.; Clarke, D. E. N-aryloxyalkyl tryptamine alpha 1-adrenergic receptor antagonists. US5436264 (A), July 25, 1995.
57. Tsotinis, A.; Panoussopoulou, M.; Sivananthan, S.; Sugden, D. Il Farm. 2001, 56, 725
58. Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Org. Chem. 1987, 52, 3404
59. Qian, D. C.; Alford, P. E.; Kishbaugh, T. L. S.; Jones, S. T.; Gribble, G. W. ARKIVOC 2010, iv, 66