A new entry to the synthesis of 2,3-disubstituted indoles

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5793-5796

  Mukai, Chisato ^a   Takahashi, Yukie ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; INDOLE ALKALOID; INDOLE DERIVATIVE; INDOMETACIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALKENES; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLE ALKALOIDS; INDOLES; INDOMETHACIN; MOLECULAR STRUCTURE;

EID: 30144432668     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052179u     Document Type: Article

References (56)

1. (a) Sundberg, R. J. Indoles; Academic Press: London, 1996.
2. (b) Joule, J. A.; Mills, K. Heterocyclic Chemistry; Blackwell Science: Oxford, 2000.
3. (a) Joule, J. A. In Science of Synthesis; Thomas, E. J., Ed.; Thieme: Stuttgart, 2000; Vol. 10.
4. (b) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
5. (c) Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148-180.
6. (a) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry; Stanley Thornes Ltd.: Cheltenham, 1995.
7. (b) Gilchrist, T. L. Heterocyclic Chemistry; Addison-Wesley Longman Limited: Singapore, 1997.
8. (c) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491-2515.
9. Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: New York, 1982.
10. For recent reviews, see: (a) Larock, R. C. J. Organomet. Chem. 1999, 576, 111-124.
11. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309.
12. (c) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
13. (c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873-2920.
14. For selected references, see: (a) Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277-4278.
15. (b) Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963-5966.
16. (c) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799-1802.
17. (d) Kondo, Y.; Sakamoto, T.; Yamanaka, H. Heterocydes 1989, 29, 1013-1016.
18. (e) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581-2584.
19. (f) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866.
20. (g) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289-296.
21. (h) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437-452.
22. (i) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803-11812.
23. (j) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366.
24. (k) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001-1011.
25. (1) Yasuhara, A.; Takeda, Y.; Suzuki, N.; Sakamoto, T. Chem. Pharm. Bull. 2002, 50, 235-238.
26. (m) Sun, P.-L.; Huang, X.-H.; Dai, W.-M. Tetrahedron 2004, 60, 10983-10992.
27. (n) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Synthesis 2004, 1889-1894 and references therein.
28. For selected references, see: (a) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305-1308.
29. (b) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
30. (c) Wensbo, D.; Eriksson, A.; Jeschke, T.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 2823-2826.
31. (d) Jeschke, T.; Wensbo, D.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 6471-6474.
32. (e) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662.
33. (f) Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 1594-1595.
34. (g) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017-8028.
35. (h) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673.
36. (i) Liu, X.; Deschamp, J. R.; Cook, J. M. Org. Lett. 2002, 4, 3339-3342.
37. (j) Hiroya, K.; Matsumoto, S.; Sakamoto, T. Org. Lett. 2004, 6, 2953-2956.
38. (k) Shen, M.; Li, G.; Lu, B. Z.; Hossain, A.; Roschangar, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2004, 6, 4129-4132.
39. (l) Konno, T.; Chae, J.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2004, 69, 8258-8265.
40. (m) Ackermann, L. Org. Lett. 2005, 7, 439-442 and references therein.
41. Upon treatment with NaH at room temperature, N-(tert-butoxycatbonyl)-2- (1-phenylsulfonylpropa-1,2-dien-1-yl)aniline underwent the endomode ring-closing reaction to furnish the corresponding indole derivative in a high yield. Mukai, C.; Kobayashi, M.; Kubota, S.; Takahashi, Y.; Kitagaki, S. J. Org. Chem. 2004, 69, 2128-2136.
42. For leading references, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
43. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
44. 3-position, which must be useful for further elaborations such as the carbon homologation reaction, if the reaction proceeded as planned.
45. All allenes used in this study were prepared by the method of Marshall, see: (a) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1992, 57, 1242-1252.
46. (b) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214-8219.
47. (c) Williams, D. R.; Mi, L.; Mullins, R. J.; Stites, R. E. Tetrahedron Lett. 2002, 43, 4841-4844.
48. 3.
49. When 10 equiv of LiCl was added to the reaction mixture (3.5 h at room temperature), 3a was obtained in 67% yield as the sole product.
50. When N-acetyl-2-iodoaniline was exposed to conditions A or B, the corresponding allenyl derivative or indole derivative was selectively formed in the respective yields of 80% and 70%, although a higher reaction temperature (50°C) was necessary under conditions A.
51. 3 effected the ring-closing reaction to produce the N-acetyl congener of 3a in 49% yield.
52. Compound 4a could be converted into 1-(terf-butoxycarbonyl)-3- hydroxymethyl-2-methylindole (desilylated-3a) in 66% yield by exposure to TBAF.
53. The use of TBAF in place of TBAC in the palladium-catalyzed coupling reaction (conditions B) was unfortunately found to be fruitless.
54. (a) Shen, T. Y.; Ellis, R. L.; Windholz, T. B.; Matzuk, A. R.; Rosegay, A.; Lucas, S.; Witzel, B. E.; Stammer, C. H.; Wilson, A. N.; Holly, F. W.; Willett, J. D.; Sarett, L. H.; Holtz, W. J.; Risley, E. A.; Nuss, G. W.; Winter, C. A. J. Am. Chem. Soc. 1963, 85, 488-489.
55. (b) Yamamoto, H. Chem. Pharm. Bull. 1968, 16, 17-19.
56. Prepared by the condensation of 2-iodo-4-methoxyaniline with 4-chlorobenzoyl chloride in 81% yield under the conventional conditions.