Halogen-metal exchange/cyclization of iodoketones: A direct synthesis of 3-arylbenzofurans

Synlett

Volumn , Issue 16, 2005, Pages 2504-2506

  Kraus, George A ^a   Schroeder, Jacob D ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Arylbenzofuran; Benzofuran; Halogen metal exchange cyclization reaction

Indexed keywords

BENZOFURAN DERIVATIVE; HALOGEN; IODOKETONE; KETONE DERIVATIVE; METAL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 26844447224     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872690     Document Type: Article

References (27)

1. (a) McCallion, G. D. Curr. Org. Chem. 1999, 3, 67.
2. (b) Comprehensive Heterocyclic Chemistry, Vol. 4; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 531.
3. (a) Babu, V. H.; Kumar, P. S.; Srinivasan, K. K.; Bhat, G. V. Indian J. Pharm. Sci. 2004, 66, 647.
4. (b) Hayakawa, I.; Shioya, R.; Agatsuma, T.; Furukawa, H.; Sugano, Y. Bioorg. Med. Chem. Lett. 2004, 14, 3411.
5. Abdel-Kader, M. S. Planta Med. 2001, 67, 388.
6. Rahim, R. T.; Meissler, J. J. Jr.; Cowan, A.; Rogers, T. J.; Geller, E. B.; Gaughan, J.; Adler, M. W.; Eisenstein, T. K. Internat. Immunopharmacol. 2001, 1, 2001.
7. (a) Frahm, A. W.; Muangnoicharoen, N. Phytochem. 1981, 20, 291.
8. (b) For a synthesis, see: Mukherjee, S. K.; Walia, S.; Kulshrestha, S. K. Tetrahedron 1986, 42, 4817.
9. Shirota, O.; Pathak, V.; Sekita, S.; Satake, M.; Nagashima, Y.; Hirayama, Y.; Hakamata, Y.; Hayashi, T. J. Nat. Prod. 2003, 66, 1128.
10. (a) Mustafa, A. In Chemistry of Heterocyclic Compounds, Vol. 29; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1974, 1-514.
11. (b) Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 259.
12. (c) Hou, H.-L.; Yang, Z.; Wong, H. N. C. Furans and Benzofurans, In Progress in Heterocyclic Chemistry, Vol. 14; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: Oxford, 2002, 139-179.
13. (a) Nicolaou, K. C.; Snyder, S. A.; Bigot, A.; Pfefferkorn, J. Angew. Chem. Int. Ed. 2000, 39, 1093.
14. (b) Habermann, J.; Ley, S. V.; Smits, R. J. Chem. Soc., Perkin Trans, 1 1999, 2421.
15. Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687.
16. Tae, J.; Kim, K.-O. Synthesis 2005, 387.
17. (a) Twyman, L. J.; Allsop, D. Tetrahedron Lett. 1999, 40, 9383.
18. (b) Fürstner, A.; Jumbam, D. N. Tetrahedron 1992, 48, 5991.
19. Kraus, G. A.; Kim, I. Org. Lett. 2003, 5, 1191.
20. Kihara, M.; Yasumasa, I.; Yoshimitsu, N. Heterocycles 1995, 41, 2279.
21. 4: 284.1048; found: 284.1053.
22. Barrero, A.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron 1998, 54, 5635.
23. Colobert, F.; Broutin, P.-E.; Castanet, A.-S. Tetrahedron Lett. 2002, 43, 5047.
24. Jackson, A. H.; Martin, J. A. J. Chem. Soc. C 1966, 23, 2222.
25. (a) Rigo, B.; Waterlot, C.; Couturier, D.; De Backer, M. Can. J. Chem. 2000, 78, 1242.
26. (b) Bringmann, G.; Pabst, T.; Henschel, P.; Michel, M. Tetrahedron 2001, 57, 1269.
27. (c) Gevorgyan, V.; Yamamoto, Y.; Rubin, M.; Benson, S.; Liu, J.-X. J. Org. Chem. 2000, 65, 6179.