A silver-catalyzed domino route toward 1,2-dihydroquinoline derivatives from simple anilines and alkynes

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2675-2678

  Luo, Yumei ^a   Li, Zigang ^a   Li, Chao Jun ^a,b  

^a Tulane University   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 29844454802     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050826b     Document Type: Article

References (56)

1. (a) Ramesh, M.; Moham, P. S.; Shanmugam, P. Tetrahedron 1984, 40, 4041.
2. (b) Witherup, K. M.; Ransom, R. W.; Varga, S. L.; Pitzenberger, S. M.; Lotti, V. J.; Lumma, W. J. U.S. Patent 5,288,725, 1994.
3. (c) Perry, N. B.; Blunt, J. W.; McCombs, J. D.; G. Munro, M. H. J. Org. Chem. 1986, 51, 5476.
4. (d) Williamson, N. M.; March, P. R.; Ward, A. D. Tetrahedron Lett. 1995, 36, 7721.
5. (e) Johnson, J. V.; Rauckman, S.; Baccanari, P. D.; Roth, B. J. J. Med. Chem. 1989, 32, 1942.
6. (f) Biller, S. A.; Misra, R. N. U.S. Patent 4,843,082, 1989.
7. (g) Mohamed, E. A. Chem. Pap. 1994, 48, 261;
8. Chem. Abstr. 1995, 123, 9315.
9. (h) Caling, R. W.; Leeson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1992, 35, 1942.
10. (i) Carling, R. W.; Leeson, P. D.; Moseley, A. M.; Smith, J. D.; Saywell, K.; Trickelbank, M. D.; Kemp, J. A.; Marshall, G. R.; Foster, A. C.; Grimwood, S. Bioorg. Med. Chem. Lett. 1993, 3, 65.
11. (j) Cuny, G. D.; Hauske, J. D.; Hoemann, M. Z.; Rossi, R. F.; Xie, R. L. PCT Int. Appl. WO 9967238, 1999; Chem. Abstr. 1999, 132, 64182.
12. (k) Hanada, K.; Furuya, K.; Inoguchi, K.; Miyakawa, M.; Nagata, N. PCT Int. Appl. WO 0127086, 2001; Chem. Abstr. 2001, 134, 295752.
13. Nesterova, I. N.; Alekseeva, L. M.; Golovira, S. M.; Granik, V. G. Khim.-Farm. Zh. 1995, 29, 31;
14. Chem. Abstr. 1996, 124, 117128t.
15. Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. Biochem. Pharmacol. 1992, 44, 1211.
16. Faber, K.; Stueckler, H.; Kappe, T. J. Heterocycl. Chem. 1984, 21, 1177.
17. Akhmed, K. S.; Bessonova, I. A. Dokl. Akad. Nauk Uzh. SSR 1982, 34;
18. Chem. Abstr. 1983, 98, 83727q.
19. (a) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656.
20. (b) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
21. (c) Povarov, L. S. Russ. Chem. Rev. Engl. Transl. 1967, 36, 656.
22. (d) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987; Chapters 2 and 9.
23. (a) Zhang, J. H.; Li, C.-J. J. Org. Chem. 2002, 67, 3969.
24. (b) Li, Z.; Zhang, J. H.; Li, C.-J. Tetrahedron Lett. 2003, 44, 153.
25. (c) Chen, L.; Li, Z. G.; Li, C. J. Synlett 2003, 5, 732.
26. (a) Skraup, Z. H. Ber. 1880, 13, 2086.
27. (b) Wahren, M. Tetrahedron 1964, 20, 2773.
28. (c) Bischler, A.; Napieralski, B. Ber. 1893, 26, 1903.
29. (d) Fodor, G.; Nagubandi, S. Tetrahedron 1980, 36, 1279.
30. Taylor, E. C.; Macor, J. E.; French, L. G. J. Org. Chem. 1991, 56, 1807.
31. Aiduini, A.; Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. Synthesis 1981, 975.
32. Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813.
33. Theeraladanon, C.; Arisawa, M.; Nishida, A.; Nakagawa, M. Tetrahedron 2004, 60, 3017.
34. (a) Hennion, G. F.; Hanzel, R. S. J. Am. Chem. Soc. 1960, 82, 4908.
35. (b) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
36. (c) Williamson, N. M.; Ward, A. D. Tetrahedron 2005, 61, 155.
37. (a) Trost, B. M. Science 1991, 254, 1471.
38. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
39. For recent examples of the hydroamination of alkynes, see: (a) Heutling, A.; Pohlki, F.; Doye, S. Chem. Eur. J. 2004, 10, 3059 and references therein.
40. (b) Illack, A.; Jiao, H.; Castro, I. G.; Hartung, C. G.; Beller, M. Chem. Eur. J. 2004, 10, 2409.
41. (c) Pohlki, F.; Bytschkov, I.; Siebeneicher, H.; Heutling, A.; Koenig, W. A.; Doye, S. Eur. J. Org. Chem. 2004, 1967.
42. (d) Anderson, L. L.; Arnold, J.; Bergman, R. G. Org. Lett. 2004, 6, 2519.
43. (e) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
44. (f) Lutete, L. M.; Kadaoto, I.; Yammaoto, Y. J. Am. Chem. Soc. 2004, 126, 1622.
45. (g) Li, Y.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794.
46. For early transition metal/lanthanide catalyzed hydroamination, see: (h) Bürgstein, M. R.; Berberich, H.; Roesky, P. W. Chem. Eur. J. 2001, 7, 3078.
47. (i) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
48. (j) Hong, S.; Marks, T. J. J. Am. Chem. Soc. 2002, 124, 7886.
49. For Ag- and Au-catalyzed hydroamination, see: (k) Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
50. (l) Robinson, R. S.; Dovey, M. C.; Gravestock, D. Eur. J. Org. Chem. 2005, 505.
51. (m) Robinson, R. S.; Dovey, M. C.; Gravestock, D. Tetrahedron Lett. 2004, 45, 6787.
52. To avoid deuterium and hydrogen exchange during the prolonged reaction time, this model study was carried out under microwave irradiation at 140°C with 100 W operating power for 20 min.
53. (a) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
54. (b) Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443.
55. 1,2-Dihydro-2-metnyl-2,4-diphenylquinoline is not stable under the current reaction conditions, and the yield is lower than starting from aniline and phenylacetylene directly.
56. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.