Iodine-catalyzed amination of benzoxazoles: A metal-free route to 2-aminobenzoxazoles under mild conditions

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 7938-7944

  Lamani, Manjunath ^a   Prabhu, Kandikere Ramaiah ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZOLE; C-H BOND; ENVIRONMENTALLY BENIGN; HIGH YIELD; PRIMARY AMINES; REACTION CONDITIONS; TERT-BUTYLHYDROPEROXIDE; TERTIARY BUTANOL; USER-FRIENDLY METHODS;

AMINATION; INDUSTRIAL CHEMICALS; IODINE;

AMINES;

2 AMINOBENZOXAZOLE DERIVATIVE; AMINE; BENZOXAZOLE DERIVATIVE; CARBON; HYDROGEN; IODINE; NITROGEN; TERT BUTYL ALCOHOL; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG; WATER;

AMINATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; ENVIRONMENTAL TEMPERATURE; HYDROGEN BOND; OXIDATION; SYNTHESIS;

ACETIC ACIDS; AMINATION; BENZOXAZOLES; CATALYSIS; GREEN CHEMISTRY TECHNOLOGY; IODINE;

EID: 80054115038     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201402a     Document Type: Article

References (40)

1. see: (a) Delord, W. J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
2. (b) Cho, S. H.; Kim J. Y.; Kwak. J, Chang S Chem. Soc. Rev. 2011, DOI: 10.1039/c1cs15082k.
3. (c) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
4. (d) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
5. (e) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
6. (f) Armstrong, A.; Collins, J. C. Angew. Chem., Int. Ed. 2010, 49, 2282.
7. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
8. (b) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
9. (c) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
10. (a) Ullmann, F. Ber. Dtsch. chem. Ges. 1903, 36, 2382.
11. (b) Gauthier, S.; FrOchet, J. M. J. Synthesis 1987, 383.
12. (c) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
13. (d) Lang, F.; Zewge, D.; Houpis, I. N.; Volante, R. P. Tetrahedron Lett. 2001, 42, 3251.
14. (a) Goldberg, I. Ber. Dtsch. chem. Ges. 1906, 39, 1691.
15. (b) Freeman, H. S.; Butler, J. R.; Freedman, L. D. J. Org. Chem. 1978, 43, 4975.
16. (c) Dharmasena, P. M.; Oliveira-Campos, A. M.-F.; Raposo, M. M. M.; Shannon, P. V. R. J. Chem. Res., Synop. 1994, 296.
17. (d) Lange, J. H. M.; Hofmeyer, L. J. F.; Hout, F. A. S.; Osnabrug, S. J. M.; Verveer, P. C.; Kruse, C. G.; Feenstra, R. W. Tetrahedron Lett. 2002, 43, 1101.
18. (a) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
19. (b) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
20. (c) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem. Int. Ed. 2009, 48, 1114.
21. (a) Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900.
22. (b) Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607.
23. (c) Wang, Q.; Schreiber, S. L. Org. Lett. 2009, 11, 5178.
24. (d) Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 2860.
25. (a) Cho, S. H.; Kim, J. Y.; Lee, S. Y.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 9127.
26. (b) Wang, J.; Hou, J.-T.; Wen, J.; Zhanga, J.; Xiao, Q, Y Chem. Commun. 2011, 47, 3652.
27. (c) Li, Y.; Xie, Y.; Zhang, R.; Kun, J.; Wang, X.; Duan, C. J. Org. Chem. 2011, 76, 5444.
28. (d) Guo, S.; Qian, B.; Xie, Y.; Xia, C.; Huang, H. Org. Lett. 2011, 13, 522.
29. (e) Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899.
30. (a) Joseph, J.; Kim, Y. J.; Chang, S. Chem.-Eur. J. 2011, 17, 8294.
31. (b) Froechr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.; Nachtsheim, B. J. Org. Lett. 2011, 13, 3754.
32. (a) Lamani, M.; Prabhu, K. R. Angew. Chem., Int. Ed. 2010, 49, 6622.
33. (b) Maddani, M.; Prabhu, K. R. J. Org. Chem. 2010, 75, 2327.
34. (c) Maddani, M.; Prabhu, K. R. Tetrahedron Lett. 2008, 49, 4526.
35. (a) Yasuo, S.; Megumi, Y.; Satoshi, Y.; Tomoko, S.; Midori, I.; Tetsutaro, N.; Kokichi, S.; Fukio, K. J. Med. Chem. 1998, 41, 3015.
36. (b) Yoshida, S; Shiokawa, S; Kawano, K.-I.; Ito, T.; Murakami, H.; Suzuki, H.; Yasuo, S. J. Med. Chem. 2005, 48, 7075.
37. (c) Gao, M.; Wang, M.; Hutchins, G.; D; Zheng, Q.-H. Eur. J. Med. Chem. 2008, 43, 1570.
38. Cioffi, C. L.; Lansing, J. J.; Yüksel, H. Y. J. Org. Chem. 2010, 75, 7942.
39. Lok, R.; Leone, R. E.; Williams, A. J. J. Org. Chem. 1996, 61, 3289.
40. Martínez-Barrasa, V.; Delgado, F.; Burgos, C.; García Navío, J. L.; Izquierdo, M. L.; Alvarez-Builla, J. Tetrahedron 2000, 56, 2481.