Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles

Tetrahedron Letters

Volumn 53, Issue 32, 2012, Pages 4232-4234

  Prabhu, Girish ^a   Sureshbabu, V V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Desulfurization; Hypervalent iodine reagent; IBX; Oxadiazole

Indexed keywords

HYDRAZIDE DERIVATIVE; IODINE DERIVATIVE; IODINE(V); IODOBENZOIC ACID DERIVATIVE; OXADIAZOLE DERIVATIVE; THIOSEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL STRUCTURE; CYCLIZATION; DESULFURIZATION; METHODOLOGY; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84863617664     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.154     Document Type: Article

References (49)

1. Z.M. Nofal, H.H. Fahmy, and H.S. Mohamed Arch. Pharm. Res. 25 2002 28
2. S.G. Kuecuekguezel, I. Kuecuekguezel, E. Tatar, S. Rollas, F. Ş ahin, M. Guelluece, E.D. Clercq, and L. Kabasakal Eur. J. Med. Chem. 42 2007 893
3. X. Ouyang, E.L. Piatnitski, V. Pattaropong, X. Chen, H.Y. He, A.S. Kiselyov, A. Velankar, J. Kawakami, M. Labelle, L. Smith, J. Lohman, S.P. Lee, A. Malikzay, J. Fleming, J. Gerlak, Y. Wang, R.L. Rosler, K. Zhou, S. Mitelman, M. Camara, D. Surguladze, J.F. Doody, and M.C. Tuma Bioorg. Med. Chem. Lett. 16 2006 1191
4. A.S. Kiselyov, M.N. Semenova, N.B. Chernyshova, A. Leitao, A.V. Samet, K.A. Kislyi, M.M. Raihstat, T. Oprea, H. Lemcke, M. Lantow, D.G. Weiss, N.N. Ikizalp, S.A. Kuznetsov, and V.V. Semenov Eur. J. Med. Chem. 45 2010 1683
5. H.L. Yale, and K. Losee J. Med. Chem. 9 1966 478
6. D. Ghirian, I. Schwatz, and I. Simiti Farmacia 22 1974 141
7. M.J. Fray, K. Cooper, M.J. Parry, K. Richardson, and J. Steele J. Med. Chem. 38 1995 3514
8. R.S. Lamani, G. Nagendra, and V.V. Sureshbabu Tetrahedron Lett. 51 2010 4705
9. J. Kosmrlj, M. Kocevar, and S. Polanc Synlett 1996 652
10. R. Mazurkiewicz, and M. Grymel Pol. J. Chem. 71 1997 77
11. C.T. Brain, J.M. Paul, Y. Loong, and P.J. Okaley Tetrahedron Lett. 40 1999 3275
12. C.T. Brain, and S.A. Brunton Synlett 2001 382
13. R.M. Shaker, A.F. Mahmoud, and F.F. Abdel-Latif Phosphorus, Sulfur and Silicon 180 2005 397
14. I.R. Baxendale, S.V. Ley, and M. Martinelli Tetrahedron 61 2005 5323
15. J. Dumciute, V. Martynaitis, W. Holzer, S. Mangelinckx, N.D. Kimpe, and A. Sackus Tetrahedron 62 2006 3309
16. S. Sharma, V.K. Srivastava, and A. Kumar Eur. J. Med. Chem. 37 2002 689
17. J. Dumciute, V. Martynaitis, W. Holzer, S. Manelinckx, N. De Kimpe, and A.S. Sackus Tetrahedron 62 2006 3309
18. S.M.S. Atta, N.M. Fawzy, F.A. Ahmed, and A.H. Abdel-Rahman Phosphorus, Sulfur and Silicon 177 2002 863
19. X.C. Wang, Z. Li, B.G. Wei, and J.Y. Yang Synth. Commun. 32 2002 1097
20. A. Zarghi, Z. Hajimahdi, S. Mohebbi, H. Rashidi, S. Mozaffari, S. Sarraf, M. Faizi, S.A. Tabatabaee, and A. Shafíee Chem. Pharm. Bull. 56 2008 509
21. S.J. Dolman, F. Gosselin, P.D. O'Shea, and I.W. Davies J. Org. Chem. 71 2006 9548
22. J.Y. Hwang, H.S. Choi, D.H. Lee, and Y.D. Gong J. Comb. Chem. 7 2005 816
23. R. Severinsen, J.P. Kilburn, and J.F. Lau Tetrahedron 61 2005 5565
24. E.L. Piatnitski Chekler, H.M. Elokdah, and J. Butera Tetrahedron Lett. 49 2008 6709
25. Y. Xie, J. Liu, P. Yang, X. Shi, and J. Li Tetrahedron 67 2011 5369
26. S.J. Dolman, F. Gosselin, P.D. O'Shea, and I.W.J. Davies Org. Chem. 2006, 71, 9548. (b) Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G Tetrahedron Lett. 45 2004 3257
27. A. Varvoglis Hypervalent Iodine in Organic Synthesis 1997 Academic Press London
28. T. Wirth Hypervalent Iodine Chemistry 2003 Springer Berlin
29. P.J. Stang, and V.V. Zhdankin Chem. Rev. 96 1996 1123
30. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523
31. H. Tohma, and Y. Kita Adv. Synth. Catal. 346 2004 111
32. G.F. Koser Adv. Heterocycl. Chem. 86 2004 225
33. R.M. Moriarty J. Org. Chem. 70 2005 2893
34. T. Wirth Angew. Chem., Int. Ed. 44 2005 3656
35. U. Ladziata, and V.V. Zhdankin ARKIVOC ix 2006 26
36. M. Ochiai Chem. Rec. 7 2007 12
37. Y. Kita, and H. Fujioka Pure Appl. Chem. 79 2007 701
38. V.V. Zhdankin, and P. Stang J. Chem. Rev. 108 2008 5299
39. M. Ochiai, and K. Miyamoto Eur. J. Org. Chem. 2008 4229
40. V.V. Zhdankin ARKIVOC i 2009 1
41. C.B. Singh, H. Ghosh, S. Murru, and B.K. Patel J. Org. Chem. 73 2008 2924
42. H. Ghosh, R. Yella, J. Nath, and B.K. Patel Eur. J. Org. 2008 6189
43. H. Ghosh, R. Yella, A.R. Ali, S.K. Sahoo, and B.K. Patel Tetrahedron Lett. 50 2009 2407
44. C. Zhu, D. Xu, and Y. Wei Synthesis 2011 711
45. P.S. Chaudhari, P.S. Dangate, and K.G. Akamanchi Synlett 2010 3065
46. For reviews on IBX, see T. Wirth Angew. Chem., Int. Ed. 40 2001 2812
47. I. Kumar Synlett 2005 1488
48. V. Satam, A. Harad, R. Rajule, and H. Pati Tetrahedron 66 2010 7659
49. A. Duschek, and S.F. Kirsch Angew. Chem., Int. Ed. 50 2011 2