Indium(III)-catalyzed tandem reaction with alkynylbenzaldehydes and alkynylanilines to heteroaromatic compounds

Journal of Organic Chemistry

Volumn 73, Issue 13, 2008, Pages 5135-5138

  Yanada, Reiko ^a   Hashimoto, Kana ^a   Tokizane, Rie ^a   Miwa, Yoshihisa ^a   Minami, Hideki ^a   Yanada, Kazuo ^b   Ishikura, Minoru ^c   Takemoto, Yoshiji ^d  

^a HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

^c HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; HETEROAROMATIC COMPOUNDS; TANDEM REACTIONS;

INDIUM COMPOUNDS;

ALKYNE; ANILINE DERIVATIVE; AROMATIC COMPOUND; BENZALDEHYDE; CARBON; HETEROCYCLIC COMPOUND; INDIUM; LEWIS ACID; NITROGEN; PHENANTHRIDINE DERIVATIVE; PHENANTHROLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

BENZALDEHYDES; CATALYSIS; HETEROCYCLIC COMPOUNDS; INDIUM; MOLECULAR STRUCTURE; SULFANILIC ACIDS;

EID: 46849114342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800474c     Document Type: Article

References (42)

1. (a) Zhu, S.; Ruchelman, A. L.; Zhou, N.; Liu, A.; Liu, L. F.; LaVoie, E. J. Bioorg. Med. Chem. 2005, 13, 6782.
2. (b) Martínez, R.; Chacón-García, L. Curr. Med. Chem. 2005, 12, 127.
3. (c) Leonetti, C.; Amodei, S.; D'Angelo, C.; Rizzo, A.; Benassi, B.; Antonelli, A.; Elli, R.; Stevens, M. F. G.; D'Incalci, M.; Zupi, G.; Biroccio, A. Mol. Pharmacol. 2004, 66, 1138.
4. (d) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053.
5. (e) Ishikawa, T. Med. Res. Rev. 2001, 21, 61.
6. (a) Shou, W.-G.; Yang, Y.-Y.; Wang, Y.-G. J. Org. Chem. 2006, 71, 9241.
7. (b) Hilt, G.; Hess, W.; Schmidt, F. Eur. J. Org. Chem. 2005, 2526.
8. (c) Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741.
9. (d) Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605.
10. (e) Pawlas, J.; Begtrup, M. Org. Lett. 2002, 4, 2687,
11. (f) Lysén, M.; Kristensen, J. L.; Vedsø, P.; Begtrup, M. Org. Lett. 2002, 4, 257,
12. (g) Li, D.; Zhao, B.; LaVoie, E. J. J. Org. Chem. 2000, 65, 2802.
13. (h) Nakanishi, T.; Suzuki, M. Org. Lett. 1999, 1, 985.
14. (a) Su, S.; Porco, J. A., Jr J. Am. Chem. Soc. 2007, 129, 7744.
15. (b) Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462.
16. (c) Asao, N.; Iso, K.; Yudha, S. S. Org. Lett. 2006, 8, 4149.
17. (d) Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3822.
18. (e) Asao, N.; Yudha, S. S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526.
19. (a) Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
20. (b) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
21. (a) Asao, N.; Sato, K. Org. Lett. 2006, 8, 5361.
22. (b) Asao, N.; Sato, K.; Menggenbateer; Yamamoto, Y. J. Org. Chem. 2005, 70, 3682.
23. (c) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
24. (d) Dyker, G.; Hildebrandt, D.; Liu, J.; Merz, K. Angew. Chem., Int. Ed. 2003, 42, 4399.
25. (e) Asao, N.; Kasahara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2003, 42, 3504.
26. (f) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
27. Very recently, Iwasawa et al. reported the synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoate with vinyl ethers. In this report, they believe the [3 + 2]-cycloaddition mechanism is reasonable at least in platinum(II)-catalyzed benzannulation. (a) Kusama, H.; Funami, H.; Iwasawa, N. Synthesis 2007, 2014,
28. (b) Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 289.
29. (c) Straub, B. F. Chem. Commun. 2004, 1726.
30. CCDC 658463 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc. cam.ac.uk/data_request/cif.
31. (a) Zhang, D.; Liu, Z.; Yum, E. K.; Larock, R. C. J. Org. Chem. 2007, 72, 251.
32. (b) Joo, J. M.; Yuan, Y.; Lee, C. J. Am. Chem. Soc. 2006, 128, 14818.
33. (c) Zhao, J.; Hughes, C. O.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 7436.
34. (d) Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345.
35. (e) Nakamura, I.; Yamamoto, Y. Chem. Rev 2004, 104, 2127, and references cited therein,
36. (f) Nakamura, I.; Bajracharya, G. B.; Mizushima, Y.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 4328.
37. (a) Miura, K.; Fujisawa, N.; Toyohara, S.; Hosomi, A. Synlett 2006, 1883.
38. (b) Sakaki, N.; Annaka, K.; Konakahara, T. Tetrahedron Lett. 2006, 47, 631.
39. (c) Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760.
40. (d) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
41. (e) Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Shirakawa, E.; Kawakami, Y. Angew. Chem., Int. Ed. 2005, 44, 1336.
42. (f) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002.