Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5731-5736

  Yin, Yan ^a   Ma, Wenying ^a   Chai, Zhuo ^a   Zhao, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSTS; CHLORIDE MINERALS; CYCLIZATION; NUCLEOPHILES;

INDOLE DERIVATIVES; INTRAMOLECULAR HYDROAMINATION; TANDEM CYCLIZATION;

AMIDES;

CARBON; CHLORIDE; DIETHYLZINC; HALIDE; INDOLE; SULFONAMIDE; ORGANOMETALLIC COMPOUND;

ADDITION REACTION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; INTRAMOLECULAR HYDROAMINATION; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMINATION; CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; ORGANOMETALLIC COMPOUNDS; SPECTROPHOTOMETRY, INFRARED; SULFONAMIDES;

EID: 34547106553     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070681h     Document Type: Article

References (54)

1. (a) Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148.
2. (b) Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 193.
3. (c) Rahman, A.; Basha, A. Indole Alkaloids; Harwood Academic Publishers: Amsterdam, The Netherlands, 1998; p 141.
4. (d) Dewick, P. M. Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6.
5. (a) Sundlberg, R. J. Indoles; Academic: London, UK, 1996.
6. (b) Islam, M. S.; Brennan, C.; Wang, Q. W.; Hossain, M. M. J. Org. Chem. 2006, 71, 4675.
7. (c) Taber, D. F.; Tian, W. W. J. Am. Chem. Soc 2006, 128, 1058.
8. (d) Fang, Y. Q.; Lautens, M. Org. Lett. 2005, 7, 3549.
9. (a) Sakai, N.; Annaka, K.; Konakahara, T. Tetrahedron Lett. 2006, 47, 631.
10. (b) Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126.
11. (c) Hiroya, K.; Matsumoto, S.; Sakamoto, T. Org. Lett. 2004, 6, 2953.
12. (d) Kamijo, S.; Sasaki, Y.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 35.
13. (e) Koradin, C.; Dhohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
14. (a) Alfonsi, M.; Arcadi, A.; Aschi, M.; Bianchi, G.; Marinelli, F. J. Org. Chem. 2005, 70, 2265.
15. (b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
16. (c) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546.
17. (d) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Synthesis 2004, 1889.
18. (a) Yin, Y.; Zhao, G. Heterocycles 2006, 68, 23.
19. (b) Yin, Y.; Zhao, G. J. Fluorine Chem. 2007, 128, 40.
20. (a) Nakamura, M.; Ilies, L.; Otsubo, S.; Nakamura, E. Angew. Chem., Int. Ed. 2006, 45, 944.
21. (b) Nakamura, M.; Hies, L.; Otsubo, S.; Nakamura, E. Org. Lett. 2006, 8, 2803.
22. (a) Yang, C. X.; Patel, H. H.; Ku, Y. Y. Synth. Commun. 1997, 27, 2125.
23. (b) Browder, C. C.; Mitchell, M. O.; Smith, R. L.; el-Sulayman, G. Tetrahedron Lett. 1993, 34, 6245.
24. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117 and references cited therein.
25. (d) Bergman, J.; Venemalm, L. Tetrahedron 1990, 46, 6061. See the Supporting Information for experimental details.
26. (a) Forshee, P. B.; Sibert, J. W. Synthesis 2006, 756.
27. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Chemistry, 2nd ed.; Wiley-Interscience: New York, 1991.
28. (c) Yasuhara, A.; Sakamoto, T. Tetrahedron Lett. 1998, 39, 595.
29. (d) Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 9455.
30. Haskins, C. M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 599.
31. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 17, 4467.
32. Gregory, Y. Y.; Stephenson, G. A.; Mitchell, S. Tetrahedron Lett. 2006, 47, 3811.
33. (a) Baldwin, J. E. Chem. Commun. 1976, 734.
34. (b) Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Sillberman, L.; Thomas, R. C. Chem. Commun. 1976, 736.
35. Lei, A. W.; Lu, X. Y. Org. Lett. 2000, 2, 2357.
36. (a) Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8186.
37. (b) Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314.
38. (c) Li, D. P.; Guo, Y. C.; Ding, Y.; Xiao, W. J. Chem. Commun. 2006, 799.
39. (d) Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199 and references cited therein.
40. (e) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576.
41. (f) Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2005, 44, 1.
42. (a) Arcadi, A.; Bianchi, G.; Chiarini, M.; D'Anniballe, G.; Marinelli, F. Synlett 2004, 944.
43. (b) Reddy, A. V.; Ravinder, K.; Goud, T. V.; Krishnaiah, P.; Raju, T. V.; Venkateswarlu, Y. Tetrahedron Lett. 2003, 44, 6257.
44. (c) Yadav, J. S.; Abraham, S.; Reddy, B. V. S.; Sabitha, G. Synthesis 2001, 2165.
45. (d) Szmuszkovicz, J. J. Am. Chem. Soc 1957, 79, 2819.
46. (e) Noland. W. E.; Christensen, G. M.; Sauer, G. L.; Dutton, G. G. S. J. Am. Chem. Soc. 1955, 77, 456.
47. (a) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
48. (b) Nunomoto, S.; Kawakami, Y.; Yamashita, Y.; Takeuchi, H.; Eguchi, S. J. Chem. Soc., Perkin. Trans. 1 1990, 111.
49. (c) Heacock, R. A.; Kasparek, S. Adv. Heterocycl. Chem. 1969, 10, 61.
50. (d) Powers, J.; Meyer, W. P.; Parsons, T. G. J. Am. Chem. Soc. 1967, 89, 5812.
51. (a) Yang, Z.; Liu, H. B.; Lee, C. M.; Chang, H. M.; Wang, H. N. C. J. Org. Chem. 1992, 57, 7248.
52. (b) Allin, S. M.; Thomas, C. I.; Allard, J. E.; Doyle, K.; Elsegood, M. R. J. Tetrahedron Lett. 2004, 45, 7103.
53. (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359.
54. (b) Luo, F. T.; Wang, R. T. Tetrahedron Lett. 1992, 33, 6835.