Metal-free synthesis of 2-aminobenzoxazoles using hypervalent iodine reagent

Tetrahedron Letters

Volumn 54, Issue 10, 2013, Pages 1290-1293

  Wagh, Yogesh S ^a   Tiwari, Neelam J ^a   Bhanage, Bhalchandra M ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2 Aminobenzoxazoles; 2 Iodoxybenzoic acid; Benzoxazoles; C H activation; Oxidative amination

Indexed keywords

2 AMINOBENZOXAZOLE DERIVATIVE; 2 IODYLBENZOIC ACID; AMINE; BENZOIC ACID DERIVATIVE; BENZOXAZOLE DERIVATIVE; IODINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE;

EID: 84873133546     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.12.127     Document Type: Article

References (45)

1. A.D. Rodriguez, C. Ramirez, I.I. Rodriguez, and E. Gonzalez Org. Lett. 1 1999 527 530
2. J.P. Davidson, and E.J. Corey J. Am. Chem. Soc. 125 2003 13486 13489
3. A. Ricci Amino Group Chemistry from Synthesis to the Life Sciences 2008 Wiley-VCH Weinheim
4. R. Hili, and A.K. Yudin Nat. Chem. Biol. 2 2006 284 287
5. I.V. Seregin, and V. Gevorgan Chem. Soc. Rev. 36 2007 1173 1193 and references therein
6. F. Kakiuchi, and T. Kochi Synthesis 2008 3013 3039
7. G. Dyker Angew. Chem., Int. Ed. 38 1999 1698 1712
8. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
9. A. Mori, and A. Sugie Bull. Chem. Soc. Jpn. 81 2008 548 561
10. C.A. Zificsak, and D.J. Hlasta Tetrahedron 60 2004 8991 9016
11. T. Satoh, and M. Miura Chem. Lett. 36 2007 200 205
12. I.V. Seregin, and V. Gevorgan Chem. Soc. Rev. 36 2007 1173 1193
13. S. Yasuo, Y. Megumi, Y. Satoshi, S. Tomoko, I. Midori, N. Tetsutaro, S. Kokichi, and K. Fukio J. Med. Chem. 41 1998 3015 3021
14. S. Yoshida, S. Shiokawa, K.-I. Kawano, T. Ito, H. Murakami, H. Suzuki, and S. Yasuo J. Med. Chem. 48 2005 7075 7079
15. M. Gao, M. Wang, G.D. Hutchins, and Q.-H. Zheng Eur. J. Med. Chem. 43 2008 1570 1574
16. Y. Sato, M. Imai, K. Amano, K. Iwamatsu, F. Konno, Y. Kurata, S. Sakakibara, M. Hachisu, M. Izumi, N. Matsuki, and H. Saito Biol. Pharm. Bull. 20 1997 752 755
17. M. Verderame J. Med. Chem. 15 1972 693 694
18. M.W. Hooper, M. Utsunomiya, and J.F. Hartwig J. Org. Chem. 68 2003 2861 2873
19. M.S.R. Murty, K.R. Ram, R.V. Rao, J.S. Yadav, U.S.N. Murty, and K.P. Kumar Med. Chem. Res. 20 2011 626 636
20. S.H. Cho, J.Y. Kim, S.Y. Lee, and S. Chang Angew. Chem., Int. Ed. 48 2009 9127 9130
21. J.Y. Kim, S.H. Cho, J. Joseph, and S. Chang Angew. Chem., Int. Ed. 49 2010 9899 9903
22. J. Wang, J.-T. Hou, J. Wen, J. Zhang, and X.-Q. Yu Chem. Commun. 47 2011 3652 3654
23. D. Monguchi, T. Fujiwara, H. Furukawa, and A. Mori Org. Lett. 11 2009 1607 1610
24. Q. Wang, and S.L. Schreiber Org. Lett. 11 2009 5178 5180
25. T. Kawano, K. Hirano, T. Satoh, and M. Miura J. Am. Chem. Soc. 132 2010 6900 6901
26. Y. Li, Y. Xie, R. Zhang, K. Jin, X. Wang, and C. Duan J. Org. Chem. 76 2011 5444 5449
27. T. Froehr, C.P. Sindlinger, U. Kloeckner, P. Finkbeiner, and B.J. Nachtsheim Org. Lett. 13 2011 3754 3757
28. M. Lamani, and K.R. Prabhu J. Org. Chem. 76 2011 7938 7944
29. S. Wertz, S. Kodama, and A. Studer Angew. Chem., Int. Ed. 50 2011 11511 11515
30. Y.S. Wagh, D.N. Sawant, and B.M. Bhanage Tetrahedron Lett. 53 2012 3482 3485
31. J. Joseph, Y.J. Kim, and S. Chang Chem. Eur. J. 17 2011 8294 8298
32. F.F. Paintner, L. Allmendinger, and G. Bauschke Synthesis 2001 2113 2118
33. S. Kirsch, and T. Bach Angew. Chem., Int. Ed. 42 2003 4685 4687
34. J.D. More, and N.S. Finney Synlett 2003 1307 1310
35. J.M. VanderRoest, and P.A. Grieco J. Org. Chem. 61 1996 5316 5325
36. F. Lach, and C.J. Moody Tetrahedron Lett. 41 2000 6893 6896
37. J.M. Bueno, J.M. Coteron, J.L. Chiara, A. Fernandez-Mayoralas, J.M. Fiandor, and N. Valle Tetrahedron Lett. 41 2000 4379 4382
38. D. Weigelt, R. Krahmer, K. Bruschke, L. Hennig, M. Findeisen, D. Muller, and P. Welzel Tetrahedron 55 1999 687 698
39. M.A. Gonzalez Tetrahedron 64 2008 445 467
40. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523 2584
41. V.V. Zhdankin Curr. Org. Synth. 2 2005 121 145
42. P.J. Stang, and V.V. Zhdankin Chem. Rev. 96 1996 1123 1178
43. J. Zhu, A.R. Germain, and J.A. Porco Jr. Angew. Chem., Int. Ed. 43 2004 1239 1243
44. M.J. Dixon, O.A. Andersen, D.M.F. van Aalten, and I.M. Eggleston Eur. J. Org. Chem. 2006 5002 5006
45. K.C. Nicolaou, T. Montagnon, P.S. Baran, and Y.L. Zhong J. Am. Chem. Soc. 124 2002 2245 2258