A concise synthesis of all four possible benzo[4,5]furopyridines via palladium-mediated reactions

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2201-2203

  Yue, Wen Song ^a   Li, Jie Jack ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; CHLORINE; PALLADIUM; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BENZOFURANS; CATALYSIS; CHLORINE; PALLADIUM; PYRIDINES;

EID: 0037182723     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0260425     Document Type: Article

References (45)

1. (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, 2000.
2. (b) Li, J. J. In Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1999; Vol. 14, pp 437-503.
3. (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
4. (d) Godard, A.; Marsais, F.; Plé, N.; Trecourt, F.; Turck, A.; Quéguiner, G. Heterocycles 1995, 40, 1055-1091.
5. (e) Undheim, K.; Benneche, T. Adv. Heterocycl. Chem. 1995, 62, 305-418.
6. (f) Kalinin, V. N. Synthesis 1992, 413-432.
7. (g) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 1155-1193.
8. (h) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1988, 27, 2225-2249.
9. Wakelin, L. P. G.; Waring, M. J. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1990, pp 703-724.
10. Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919-1925.
11. Abramovitch, R. A.; Inbasekaran, M. N.; Kato, S.; Radzikowska, T. A.; Tomask, P. J. Org. Chem. 1983, 48, 690-695.
12. Lai, L.-L.; Lin, P.-Y.; Huang, W.-H.; Shiao, M-J.; Hwu, J. R. Tetrahedron Lett. 1994, 35, 3545-3546.
13. Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998.
14. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Queguiner, G. Tetrahedron Lett. 1994, 35, 6489-6492.
15. (a) Kelly, T. R.; Li, Q.; Bhushan, V. Tetrahedron Lett. 1990, 31, 161-164.
16. (b) Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1991, 32, 3859-3862.
17. (c) Sakamoto, T.; Yasuhara, A.; Kondo, Y.; Yamanaka, H. Heterocycles 1991, 36, 2597-2600.
18. (d) Fukuyama, Y.; Yaso, H.; Nakamura, K.; Kodama, M. Tetrahedron Lett. 1999, 40, 105-108.
19. (e) Seiders, T. J.; Baldridge, K. K.; Elliott, E. L.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc. 1999, 121, 7439-7440.
20. (f) Iyoda, M.; Miura, M. L; Sasaki, S.; Kabir, S. M. H.; Kuwatani, Y.; Yoshida, M. Tetrahedron Lett. 1997, 38, 4581-4582.
21. (g) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505-1510.
22. 7NO: C, 78.09; H, 4.17; N, 8.28. Found: C, 77.96; H, 4.22: N, 8.19.
23. (a) Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140.
24. (b) Gribble, G. W.; Saulnier, M. G. Heterocycles 1993, 35, 151-169.
25. (c) Mallet, M.; Quéguiner, G. Tetrahedron 1982, 38, 3035-3042.
26. (d) Mallet, M.; Quéguiner, G. Tetrahedron 1986, 42, 2253-2262.
27. 7NO: C, 78.09; H, 4.17; N, 8.28. Found: C, 77.92; H, 4.26; N, 8.16.
28. 7NO: C, 78.09; H. 4.17; N, 8.28. Found: C, 78.02; H, 4.13; N, 8.17.
29. Cho, S. Y.; Kim, S. S.; Park, K.-H.; Kang, S. K.; Choi, J.-K.; Hwang, K.-J.; Yum, E. K. Heterocycles 1996, 43, 1641-1652.
30. (a) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683-5705.
31. (b) Harada, T.; Ueda, S.; Yoshida, T.; Inoue, A.; Takeuchi, M.; Ogawa, N.; Oku, A.; Shiro, M. J. Org. Chem. 1994, 59, 7575-7576.
32. (c) Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J. P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332.
33. (d) Barton, D. H. R.; Finet, J. P. Pure Appl. Chem. 1987, 59, 937-946.
34. (a) Bringmann, G.; Heubes, M.; Breuning, M.; Göbel, L.; Ochse, M.; Schöner, B.; Schupp, O. J. Org. Chem. 2000, 65, 722-728.
35. (b) Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313-6316.
36. (c) Hosoya, T.; Takashira, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004-1015.
37. (d) Hirayama, H.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241.
38. Jeffery's conditions: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287-1289.
39. (b) Jeffery, T. Tetrahedron Lett. 1999, 40, 1673-1676.
40. (c) Jeffery, T. Tetrahedron Lett. 1998, 39, 5751-5754.
41. (d) Jeffery, T. Adv. Met.-Org. Chem. 1996, 5, 153-260.
42. (e) Jeffery, T. Tetrahedron 1996, 52, 10113-10130.
43. (f) Jeffery, T. Tetrahedron Lett. 1994, 35, 4103-4106.
44. + + 1).
45. Li, J. J. In Progresses in Heterocvclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: Oxford, 2000; Vol. 12, pp 37-56.