Synthesis of 3-indolylarylmethanamides by samarium triiodide catalyzed Friedel-Crafts amidoalkylation

Synthesis

Volumn , Issue 16, 2008, Pages 2582-2588

  Mao, Hui ^a   Wang, Xiaoxia ^a   Wang, Wencun ^a   He, Liang ^a   Kong, Lichun ^a   Liu, Junhua ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

Amidoalkylation; Catalysis; Indoles; N ( benzotriazol 1 ylalkyl)amides; Samarium triiodide

Indexed keywords

AMIDES; CATALYST SELECTIVITY; SAMARIUM;

AMIDOALKYLATION; CATALYSIS; INDOLES; SAMARIUM TRIIODIDE;

SAMARIUM COMPOUNDS;

AMIDE; INDOLE DERIVATIVE; N [(1 BENZYL 1H INDOL 3 YL)(4 METHOXYPHENYL)METHYL]ACETAMIDE; N [(1H INDOL 3 YL)(4 NITROPHENYL)METHYL]BENZAMIDE; N [(1H INDOL 3 YL)(PHENYL)METHYL]ACETAMIDE; N [(1H INDOL 3 YL)(PHENYL)METHYL]BENZAMIDE; N [(2 METHYL 1H INDOL 3 YL)(PHENYL)METHYL]ACETAMIDE; N [(4 METHOXYPHENYL)(2 METHYL 1H INDOL 3 YL)METHYL]ACETAMIDE; N [(4 METHOXYPHENYL)(2 PHENYL 1H INDOL 3 YL)METHYL]ACETAMIDE; N [(4 METHOXYPHENYL)(4 METHYL 1H INDOL 3 YL)METHYL]ACETAMIDE; N [(4 METHOXYPHENYL)(5 METHYL 1H INDOL 3 YL)METHYL]ACETAMIDE; N [(5 BROMO 1H INDOL 3 YL)(PHENYL)METHYL]BENZAMIDE; N [(5 METHYL 1H INDOL 3 YL)(4 NITROPHENYL)METHYL]BENZAMIDE; N [(BROMO 1H INDOL 3 YL)(PHENYL)METHYL]ACETAMIDE; N [PHENYL(2 PHENYL 1H INDOL 3 YL)METHYL]ACETAMIDE; SAMARIUM; SAMARIUM TRIIODIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; SYNTHESIS;

EID: 50849112069     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067192     Document Type: Article

References (45)

1. (a) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970, 105.
2. (b) Sundberg, R. J. Indoles; Academic Press: San Diego, 1996, 113.
3. (c) Saxton, J. E. Nat. Prod. Rep. 1997, 14, 559.
4. (d) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
5. (e) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.
6. (f) Rajeswaran, W. G.; Labroo, R. B.; Cohen, L. A.; King, M. M. J. Org. Chem. 1999, 64, 1369.
7. (g) Jiang, B.; Yang, C.-G.; Wang, J. J. Org. Chem. 2001, 66, 4865.
8. (h) Wang, T.; Cook, J. M. Org. Lett. 2000, 2, 2057.
9. (i) Chataigner, I.; Hess, E.; Toupet, L.; Piettre, S. R. Org. Lett. 2001, 3, 515.
10. (j) Molina, P.; Alcantara, J.; Lopez-Leonardo, C. Tetrahedron 1996, 52, 5833.
11. (a) Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278.
12. (b) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1.
13. (c) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587.
14. (a) Mi, X. L.; Luo, S. Z.; He, J. Q.; Cheng, J. P. Tetrahedron Lett. 2004, 45, 4567.
15. (b) Xie, W.; Bloomfield, K. M.; Jin, Y.; Dolney, N. Y.; Wang, P. G. Synlett 1999, 498.
16. (c) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751.
17. (d) Shirakawa, S.; Kobayashi, S. Org. Lett. 2006, 8, 4939.
18. (a) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
19. (b) Jia, Y.; Xie, J.; Duan, H.; Wang, L.; Zhou, Q. Org. Lett. 2006, 8, 1621.
20. (c) Kang, Q.; Zhao, Z. A.; You, S. L. J. Am. Chem. Soc. 2007, 129, 1484.
21. (d) Esquivias, J.; Arrayás, R. G.; Carretero, J. C. Angew. Chem. Int. Ed. 2006, 45, 629.
22. (e) Gong, Y.; Kato, K.; Kimoto, H. Synlett 2000, 1058.
23. (f) Gong, Y. Tetrahedron: Asymmetry 2001, 12, 2121.
24. (g) Johannsen, M. Chem. Commun. 1999, 2233.
25. (h) Hao, J.; Taktak, S.; Aikawa, K.; Yusa, Y.; Hatano, M.; Mikami, K. Synlett 2001, 1443.
26. Wynne, J. H.; Stalick, W. M. J. Org. Chem. 2002, 67, 5850.
27. (a) Venkov, A. P.; Statkova-Abeghe, S. M.; Donova, A. K. Cent. Eur. J. Chem. 2004, 2, 234.
28. (b) Sheinkman, A. K.; Kucherenko, A. P. Chem. Heterocycl. Compd. 1974, 9, 1296.
29. (c) Katritzky, A. R.; Yang, Z.; Lam, J. N. Tetrahedron 1992, 48, 4971.
30. (a) Katritzky, A. R.; Drewniak, M. J. Chem. Soc., Perkin Trans. 1 1988, 2339.
31. (b) Katritzky, A. R.; Pernak, J.; Fan, W. Q.; Saczewski, F. J. Org. Chem. 1991, 56, 4439.
32. (c) Katritzky, A. R.; Drewniak, M. Tetrahedron Lett. 1988, 29, 1755.
33. Wang, X. X.; Mao, H.; Liu, J. H.; Du, J. X. Synth. Commun. 2007, 37, 3751.
34. (a) Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. J. Org. Chem. 1995, 60, 4002.
35. (b) Katritzky, A. R.; Fan, W.-Q.; Black, M.; Pernak, J. J. Org. Chem. 1992, 57, 547.
36. (c) Katritzky, A. R.; Takahashi, I.; Fan, W.-Q.; Pernak, J. Synthesis 1991, 1147.
37. Katritzky, A. R.; Pernak, J.; Fan, W. Q. Synthesis 1991, 868.
38. Katritzky, A. R.; Urogdi, L.; Mayence, A. J. Org. Chem. 1990, 55, 2206.
39. Katritzky, A. R.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555.
40. (a) Zhang, Z. H.; Yin, L.; Wang, Y. M. Synthesis 2005, 1949.
41. (b) Du, D. M.; Meng, S. M.; Wang, Y. M.; Meng, J. B.; Zhou, X. Z. Chin. J. Chem. 1995, 13, 520.
42. (c) Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609.
43. (d) Nagarajian, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229.
44. Katritzky, A. R.; Yao, G.; Lan, X.; Zhao, X. J. Org. Chem. 1993, 58, 2086.
45. Katritzky, A. R.; Kirichenko, K.; Elsayed, A. M.; Ji, Y.; Fang, Y.; Steel, P. J. J. Org. Chem. 2002, 67, 4957.