Indium trichloride catalyzed synthesis of 2-aryl-3-aminobenzofuran derivatives by a three-component reaction of phenols, arylglyoxal monohydrates and para-toluenesulfonamide

Synlett

Volumn , Issue 13, 2005, Pages 2047-2051

  Chen, Cong Xi ^a,b   Liu, Li ^a   Yang, Dong Peng ^a   Wang, Dong ^a   Chen, Yong Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Arylglyoxal monohydrate; Benzofuran; Indium trichloride; Phenol; Three component reaction

Indexed keywords

1,2 DICARBONYL DERIVATIVE; 3 AMINOBENZOFURAN; BENZOFURAN DERIVATIVE; INDIUM CHLORIDE; PHENOL DERIVATIVE; SOLVENT; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; TEMPERATURE;

EID: 23944471213     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872239     Document Type: Article

References (50)

1. (a) Cagniant, P.; Cagniant, D. Adv. Heterocycl. Chem. 1975, 18, 337.
2. (b) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209.
3. Ohemeng, K. A.; Apollina, M. A.; Ngnuyen, V. N.; Schwender, C. F.; Singer, M.; Steher, M.; Ansell, J.; Argentieri, D.; Hagemann, W. J. Med. Chem. 1994, 37, 3663.
4. Kiyama, R.; Homma, T.; Hayashi, K.; Ogawa, M.; Hara, M.; Fujimoto, M.; Fujishita, T. J. Med. Chem. 1995, 38, 2728.
5. Nagahara, T.; Yokoyama, Y.; Inamura, K.; Katakura, S.; Komoriya, S.; Yamaguchi, H.; Hara, T.; Iwamoto, M. J. Med. Chem. 1994, 37, 1200.
6. Yang, Z.; Liu, H. B.; Lee, C. M.; Chang, H. M.; Wong, H. N. C. J. Org. Chem. 1992, 57, 7248.
7. Su, T.; Naughton, M. A. H.; Smyth, M. S.; Rose, J. W.; Arfsten, A. E.; McCowan, J. R.; Jakubowski, J. A.; Wyss, V. A.; Ruterbories, K. J.; Sall, D. J.; Scarborough, R. M. J. Med. Chem. 1997, 40, 4308.
8. (a) Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700.
9. (b) Meshram, H. M.; Sekhar, K. C.; Ganesh, Y. S. S.; Yadav, J. S. Synlett 2000, 1273.
10. (c) Hu, Y. H.; Nawoschik, K. J.; Liao, Y.; Ma, J.; Fathi, R.; Yang, Z. J. Org. Chem. 2004, 69, 2235.
11. (d) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
12. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
13. (f) Willis, M. C.; Talor, D.; Gillmore, A. T. Org. Lett. 2004, 6, 4755.
14. (g) Park, K. K.; Jeong, J. Tetrahedron 2005, 61, 545.
15. (h) Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G.; Marinelli, F. Synlett 2002, 453.
16. (i) Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
17. (j) Macleod, C.; Mckiernan, G. J.; Guthrie, E. J.; Farrugia, L. J.; Hamprecht, D. W.; Macritchie, J.; Hartley, R. C. J. Org. Chem. 2003, 68, 387.
18. (k) Mckiernan, G. J.; Hartley, R. C. Org. Lett. 2003, 5, 4389.
19. (l) Katritzky, A. R.; Ji, Y.; Fang, Y. F.; Prakash, I. J. Org. Chem. 2001, 66, 5613.
20. (m) D'Sa, B. A.; Kisanga, P.; Verkade, J. G. Synlett 2001, 670.
21. (n) Lin, S. Y.; Chen, C. L.; Lee, Y. J. J. Org. Chem. 2003, 68, 2968.
22. (a) Hu, Y. H.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365.
23. (b) Li, C. C.; Xie, Z. X.; Zhang, Y. D.; Chen, J. H.; Yang, Z. J. Org. Chem. 2003, 68, 8500.
24. (c) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607.
25. (d) Wu, M. J.; Lee, C. Y.; Lin, C. F. Angew. Chem. Int. Ed. 2002, 41, 4077.
26. (e) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727.
27. (f) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
28. (g) Hu, Y. H.; Yang, Z. Org. Lett. 2001, 3, 1387.
29. (h) Cacchi, S.; Fabrizi, G.; Mero, L. Tetrahedron Lett. 1998, 39, 5101.
30. (i) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441.
31. (j) Hughes, C. C.; Trauner, D. Angew. Chem. Int. Ed. 2002, 41, 1569.
32. (a) Morice, C.; Garrido, F.; Mann, A.; Suffert, J. Synlett 2002, 501.
33. (b) Bach, T.; Bartels, M. Tetrahedron Lett. 2002, 43, 9125.
34. (c) Bach, T.; Bartels, M. Synlett 2001, 1284.
35. (d) Bach, T.; Bartels, M. Synthesis 2003, 925.
36. (a) Weber, L. Drug Discovery Today 2002, 7, 143.
37. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1993, 32, 563.
38. (c) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3169.
39. Fayol, A.; Zhu, J. P. Angew. Chem. Int. Ed. 2002, 41, 3633.
40. For the leading references on the synthesis of similar aminobenzofuran derivatives, see: (a) Ishikawa, T.; Miyahara, T.; Asakura, M.; Higuchi, S.; Miyauchi, Y.; Saito, S. Org. Lett. 2005, 7, 1211.
41. (b) Tsuji, E.; Ando, K.; Kunitomo, J. I.; Yamashita, M.; Ohta, S.; Kohno, S.; Ohishi, Y. Org. Biomol. Chem. 2003, 1, 3139.
42. (c) Ando, K.; Tsuji, E.; Ando, Y.; Kuwata, N.; Kunitomo, J. I.; Yamashita, M.; Ohta, S.; Kohno, S.; Ohishi, Y. Org. Biomol. Chem. 2004, 2, 625.
43. (d) Habermann, J.; Ley, S. V.; Smits, R. J. Chem. Soc., Perkin Trans. 1 1999, 2421.
44. (e) Viti, G.; Giannotti, D.; Nannicini, R.; Ricci, R.; Pestellini, V. J. Heterocycl. Chem. 1991, 28, 379.
45. (f) Vaidya, V. P.; Mahajan, S. B.; Agasimundin, Y. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981, 20, 391.
46. Unpublished results.
47. (a) Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270; and references cited therein.
48. (b) Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
49. Loh, T. P.; Wei, L. L. Tetrahedron 1998, 54, 7615; and references cited therein.
50. 3S: C, 71.57; H, 6.01; N, 3.34. Found: C, 71.38; H, 6.09; N, 3.13.