Iron-catalyzed intramolecular O-arylation: Synthesis of 2-aryl benzoxazoles

Organic Letters

Volumn 10, Issue 13, 2008, Pages 2665-2667

  Bonnamour, Julien ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZOXAZOLE DERIVATIVE; IRON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMIDES; BENZOXAZOLES; CATALYSIS; CYCLIZATION; IRON; MOLECULAR STRUCTURE;

EID: 50049107094     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800744y     Document Type: Article

References (42)

1. For examples in medicinal chemistry, see: (a) McKee, M. L.; Kerwin, S. M. Bioorg. Med. Chem. 2008, 16, 1775.
2. (b) Oksuzoglu, E.; Tekiner-Gulbas, B.; Alper, S.; Temiz-Arpaci, O.; Ertan, T.; Yildiz, I.; Diril, N.; Sener-Aki, E.; Yalcin, I. J. Enzyme Inhib. Med. Chem. 2008, 23, 37.
3. (c) Oksuzoglu, E.; Temiz-Arpaci, O.; Tekiner-Gulbas, B.; Eroglu, H.; Sen, G.; Alper, S.; Yildiz, I.; Diril, N.; Aki-Sener, E.; Yalcin, I. Med. Chem. Res. 2007, 16, 1.
4. (d) Potashman, M. H.; Bready, J.; Coxon, A.; DeMelfi, T. M., Jr.; DiPietro, L.; Doerr, N.; Elbaum, D.; Estrada, J.; Gallant, P.; Germain, J.; Gu, Y.; Harmange, J.-C.; Kaufman, S. A.; Kendall, R.; Kim, J. L.; Kumar, G. N.; Long, A. M.; Neervannan, S.; Patel, V. F.; Polverino, A.; Rose, P.; Van der Plas, S.; Whittington, D.; Zanon, R.; Zhao, H. J. Med. Chem. 2007, 50, 4351.
5. (e) Huang, S.-T.; Hsei, I-J.; Chen, C. Bioorg. Med. Chem. 2006, 14, 6106.
6. For example: (a) Easmon, J.; Purstinger, G.; Thies, K.-S.; Heinisch, G.; Hofmann, J. J. Med. Chem. 2006, 49, 6343.
7. (b) Sun, L.-Q.; Chen, J.; Cruce, M.; Deskus, J. A.; Epperson, J. R.; Takaki, K.; Johnson, G.; Iben, L.; Malhe, C. D.; Ryan, E.; Xu, C. Bioorg. Med. Chem. Lett. 2004, 14, 3799.
8. (c) Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Bioorg. Med. Chem. 2002, 10, 3997.
9. For example, see: (a) Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.
10. (b) Terashima, M.; Ishii, M.; Kanaoka, Y. Synthesis 1982, 484.
11. (c) Bougrin, K.; Loupy, A.; Soufiaoui, M. Tetrahedron Lett. 1998, 54, 8055.
12. (d) Chang, J.; Zhao, K.; Pan, S. Tetrahedron Lett. 2002, 43, 951.
13. (e) Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713.
14. (f) Seijas, J. A.; Vázquez-Tato, M. P.; Carballido-Reboredo, M. R.; Crecente-Campo, J.; Romar-López, L. Synlett 2007, 313.
15. (g) Seijas, J. A.; Vázquez-Tato, M. P.; Carballido-Reboredo, M. R.; Crecente-Campo, J.; Romar-López, L. Synlett 2007, 313.
16. Selected examples: (a) Sezen, B.; Sames, D. Org. Lett. 2003, 5, 3607.
17. (b) Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
18. (c) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
19. (d) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
20. (e) Downer-Riley, N. K.; Jackson, Y. A. Tetrahedron 2007, 61, 10276.
21. (a) Altenhoff, G.; Glorius, F. Adv. Synth. Catal. 2004, 346, 1661.
22. (b) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
23. (c) Barbero, N.; Carril, M.; SanMartin, R.; Domínguez, E. Tetrahedron 2007, 63, 10425.
24. (d) Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452.
25. For general overviews on iron catalyses, see: (a) Bolm, C.; Legros, J.; PaihJ. L.; Zani L, Chem. Rev. 2004, 104, 6217.
26. (b) Fürstner, A.; Martin, R. Chem. Lett. 2005, 624.
27. For selected recent iron-catalyzed carbon-heteroatom bond forming processes, see: (a) Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem., Int. Ed. 2006, 45, 2938.
28. (b) Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 6053.
29. (c) Nakanishi, M.; Bolm, C. Adv. Synth. Catal. 2007, 349, 861.
30. (d) Chen, M. S.; White, C. Science 2007, 318, 783.
31. (e) Gelalcha, F. G.; Bitterlich, B.; Anilkumar, G.; Tse, M. T.; Beller, M. Angew. Chem., Int. Ed. 2007, 46, 7293.
32. (f) Kawatsura, M.; Komatsu, Y.; Yamamoto, M.; Hayase, S.; Itoh, T. Tetrahedron Lett. 2007, 48, 6480.
33. (g) Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2008, 49, 858.
34. (a) Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862.
35. (b) Correa, A.; Bolm, A. Adv. Synth. Catal. 2008, 350, 391.
36. (c) Correa, A.; Elmore, S.; Bolm, C. Chem. - Eur. J. 2008, 14, 3527.
37. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 586.
38. Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
39. For examples of benzoxazole formations that proceeded via either aryne intermediates or aromatic substitutions, see: (a) Hrutford, B. F.; Bunnett, J. F. J. Am. Chem. Soc. 1958, 80, 2021.
40. (b) El-Sheikh, M. I.; Marks, A.; Biehl, E. R. J. Org. Chem. 1981, 46, 3256.
41. (c) Reavill, D. R.; Richardson, S. K. Synth. Commun. 1990, 20, 1423.
42. (d) Inukai, Y.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1979, 52, 2657.