A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1113-1116

  Aillaud, Isabelle ^a   Bossharth, Emmanuel ^a   Conreaux, David ^a   Desbordes, Philippe ^b   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646453634     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053048w     Document Type: Article

References (43)

1. For representative illustrations, see the following reviews: (a) Nakamura, I.; Yamamoto, Y. Chem. Rev 2004, 104, 2127.
2. (b) Zeni, G.; Larock, R. C. Chem. Rev 2004, 104, 2285.
3. (c) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev 2004, 104, 3079.
4. (d) Vizer, S. A.; Yerzhanov, K. B.; Al Aziz Al Quntar, A.; Dembitsky V. M. Tetrahedron 2004, 60, 5499.
5. For a review, see: Lomberget, T.; Bossharth, E.; Bouyssi, D.; Monteiro, N.; Balme, G. Synthesis 2003, 2407.
6. (a) Banwell, M. G.; Flynn, B. L.; Willis, A. C.; Hamel, E. Aust. J. Chem. 1999, 52, 767.
7. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
8. (c) Colobert, F.; Castanet, A.-S.; Abillard, O. Eur. J. Org. Chem. 2005, 3334.
9. (d) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
10. Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli F. Org. Lett. 2002, 4, 2409.
11. Rao, M. S.; Esho, N.; Sergeant, C.; Roman, D. J. Org. Chem. 2003, 68, 6788.
12. (a) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
13. (b) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377.
14. (a) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
15. (b) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
16. (c) Yao, D.; Yue, D.; Larock, R. C. J. Comb. Chem. 2005, 7, 809.
17. Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437
18. Yao, T.; Larock R. C. J. Org. Chem. 2005, 70, 1432.
19. (a) Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
20. (b) Yue, D.; Della Cà, N.; Larock R. C. Org. Lett. 2004, 6, 1581.
21. (a) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
22. (b) Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067.
23. Peng, A.-Y.; Ding, Y.-X. Org. Lett. 2004, 6, 1119.
24. Yao, T.; Yue, D.; Larock, R. C. J. Org. Chem. 2005, 70, 9985.
25. For other recent examples of iodonium-promoted heterocyclizations of acetylenic compounds, see: (a) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769.
26. (b) Liu, Y.; Song, F.; Cong, L. J. Org. Chem. 2005, 70, 6999.
27. (c) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679.
28. (d) Liu, Y.; Zhou, S. Org. Lett. 2005, 7, 4609.
29. (e) Waldo, J. P.; Larock R. C. Org. Lett. 2005, 7, 5203.
30. Michael, J. P. Nat. Prod. Rep. 2005, 22, 627 and previous annual reports.
31. Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441.
32. An example of such an outcome, albeit not involving activation by iodonium species, has been reported: Gaston, J. L.; Greer, R. J.; Grundon, M. F. J. Chem. Res., Miniprint 1985, 1873.
33. (a) Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642 and references therein.
34. (b) Wu, T.-S.; Li, C.-Y.; Leu, Y.-L.; Hu, C.-Q. Phytochemistry 1999, 50, 509.
35. (c) Chang, G.-J.; Wu, M.-H.; Chen, W.-P.; Kuo, S.-C.; Su, M.-J. Drug Dev. Res. 2000, 50, 170.
36. (d) Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Carroll, J. G.; Mackerracher, D.; Malone, J. F. J. Chem. Soc., Perkin Trans. 1 2000, 3397.
37. (e) Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron 2001, 57, 4719.
38. 3.
39. Sekar, M.; Rajendra Prasad, K. J. J. Nat. Prod. 1998, 61, 294.
40. Gaston, J. L.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1989, 905.
41. Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin Trans. 1 1991, 259.
42. 2 in the cyclization process.
43. See the Supporting Information. It should be noted that the 4-benzyloxypyridinium salts undergo debenzylation in the same manner. However, purification of the products required chromatography.