A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles

Tetrahedron Letters

Volumn 47, Issue 39, 2006, Pages 6983-6986

  Dabiri, Minoo ^a   Salehi, Peyman ^a   Baghbanzadeh, Mostafa ^a   Bahramnejad, Mahboobeh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,3,4 Oxadiazole; Ceric ammonium nitrate; Cyclization oxidation; Heterocycles

Indexed keywords

ALDEHYDE; HYDRAZIDE DERIVATIVE; OXADIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; POLYMERIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33747772445     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.127     Document Type: Article

References (61)

1. Tully W.R., Cardner C.R., Gillespie R.J., and Westwood R. J. Med. Chem. 34 (1991) 2060-2067
2. Chen C.Y., Senanayake C.H., Bill J., Larsen R.D., Veshoeven T.R., and Reider P.J. J. Org. Chem. 59 (1994) 3738-3741
3. Dogan H.N., Duran A., Rollas S., Sener G., Uysal M.K., and Gulen D. Bioorg. Med. Chem. 10 (2002) 2893-2898
4. Shi W., Qian X., Zhang R., and Song G. J. Agric. Food Chem. 49 (2001) 124-130
5. Chen H., Li Z., and Han Y. J. Agric. Food Chem. 48 (2000) 5312-5315
6. Meng H., and Hung W. J. Org. Chem. 65 (2000) 3894-3901
7. Bottino F.A., Pasquale G.D., and Iannelli P. Macromolecules 34 (2001) 33-37
8. Chen Z.-K., Meng H., Lai Y.-H., and Huag W. Macromolecules 32 (1999) 4351-4358
9. Perez M.A., and Bermejo J.M. J. Org. Chem. 58 (1993) 2628-2630
10. Lee D.W., Kwon K.-Y., Jin J.I., Park Y., Kim Y.-R., and Hwang I.-W. Chem. Mater. 13 (2001) 565-574
11. Diana G.D., Volkots D.L., Nitz T.J., Biailly T.R., Long M.A., Vesico N., Aldous A., Pevear D.C., and Dukto F.J. J. Med. Chem. 37 (1994) 2421-2436
12. Tandon V.K., and Chhor R.B. Synth. Commun. 31 (2001) 1727-1732
13. Liras S., Allen M.P., and Segelstein B.E. Synth. Commun. 30 (2000) 437-443
14. Carlsen H.J., and Jorgensen K.B. J. Heterocycl. Chem. 31 (1994) 805-807
15. Al-Talib M., Tashtoush H., and Odeh N. Synth. Commun. 20 (1990) 1811-1817
16. Kerr N.V., Ott D.G., and Hayes F.N. J. Am. Chem. Soc. 82 (1960) 186-189
17. Theocharis A.B., and Alexandrou N.E. J. Heterocycl. Chem. 27 (1990) 1685-1688
18. Short F.W., and Long L.M. J. Heterocycl. Chem. 6 (1969) 707
19. Park Y.-D., Kim J.-J., Chung H.-A., Kweon D.-H., Cho S.-D., Lee S.-G., and Yoon Y.-J. Synthesis (2003) 560-564
20. Bentiss F., and Lagrenee M. J. Heterocycl. Chem. 36 (1999) 1029-1032
21. Osipova T.F., Koldobskii G.I., and Ostrovskii V.A. Zh. Org. Khim. 20 (1984) 1119-1120
22. Chem. Abstr. 101 (1984) 110832j
23. Balachandran K.S., and George M.V. Tetrahedron 29 (1973) 2119-2128
24. Chiba T., and Okimoto M. J. Org. Chem. 57 (1992) 1375-1379
25. Yang R., and Dai L. J. Org. Chem. 58 (1993) 3381-3383
26. Rostamizadeh S., and Housanini G. Tetrahedron Lett. 45 (2004) 8753-8756
27. Reddy P.S.N., and Reddy P.R. Indian J. Chem. 26B (1987) 890-891
28. Ainsworth C. J. Am. Chem. Soc. 77 (1955) 1148-1150
29. Leiby R.W. J. Heterocycl. Chem. 21 (1984) 1825-1832
30. Shafiee A., Naimi E., Mansobi P., Foroumadi A., and Shekari M. J. Heterocycl. Chem. 32 (1995) 1235-1239
31. Brain C.T., and Brunton Sh.A. Synlett (2001) 382-384
32. Brown B.J., Clemens I.R., and Neesom J.K. Synlett (2000) 131-133
33. Brain C.T., Paul J.M., Loong Y., and Oakley P.J. Tetrahedron Lett. 40 (1999) 3275-3278
34. Wipf P., and Venkatraman S. Tetrahedron Lett. 37 (1996) 4659-4662
35. Kilburn J.P., Lau J., and Jones R.C.F. Tetrahedron Lett. 42 (2001) 2583-2586
36. Coppo F.T., Evans K.A., Graybill T.L., and Burton G. Tetrahedron Lett. 45 (2004) 3257-3260
37. Smith G.F., Sullivan V.R., and Frank G. Ind. Eng. Chem. Anal. Ed. 8 (1936) 449-451
38. Molander G.A. Chem. Rev. 92 (1992) 29-68
39. Hwu J.R., and King K.-Y. Curr. Sci. 81 (2001) 1043-1053
40. Hwu J.R., Shiao S.-S., and Hakimelahi G.H. Appl. Organomet. Chem. 11 (1997) 381-391 and references cited therein
41. Hwu J.R., Chen C.N., and Shaio S.-S. J. Org. Chem. 60 (1995) 826-862
42. Hwu J.R., Chen k.-L., and Ananthan S. J. Chem. Soc., Chem. Commun. (1994) 1425-1426
43. Baghbanzadeh M., Salehi P., Dabiri M., and Kozehgary Gh. Synthesis (2006) 344-348
44. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Synlett (2005) 1155-1157
45. Salehi P., Dabiri M., Zolfigol M.A., and Bodaghi Fard M.A. Tetrahedron Lett. 44 (2003) 2889-2891
46. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Heterocycles 62 (2005) 1417-1421
47. Dabiri M., Salehi P., Mohammadi A.A., and Baghbanzadeh M. Synth. Commun. 35 (2005) 279-287
48. Dabiri M., Salehi P., Otokesh S., Baghbanzadeh M., Kozehgary Gh., and Mohammadi A.A. Tetrahedron Lett. 46 (2005) 6123-6126
49. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Tetrahedron Lett. 46 (2005) 7051-7053
50. Salehi P., Dabiri M., Zolfigol M.A., Otokesh S., and Baghbanzadeh M. Tetrahedron Lett. 47 (2006) 2557-2560
51. Rao V.S., and Chandra Sekhar K.V.G. Synth. Commun. 34 (2004) 2153-2157
52. Kingston D.G.I., and Tannenbaum H.P. J. Chem. Soc. C (1970) 2574
53. Gilbert E.C. J. Am. Chem. Soc. 49 (1927) 286-292
54. Agarwal J.S. Chem. Ber. 35 (1929) 1941
55. Uher M., and Foltin J. Collect. Czech. Chem. Commun. 46 (1981) 1492-1494
56. Milcent R. J. Heterocycl. Chem. 20 (1983) 77-80
57. Huisgen R., Sauer J., and Markgraf J.H. Chem. Ber. 93 (1960) 2106-2124
58. Mashraqui S.H., Ghadigaonkar Sh.G., and Kenny R.S. Synth. Commun. 33 (2003) 2541-2545
59. Khajavi M.S., Sadat Hosseini S.S., and Sefidkon F. Iran. J. Chem. Chem. Eng. 16 (1997) 68-71
60. Khan M.T.H., Choudhary M.I., Khan K.M., Rani M., and Rahman A. Bioorg. Med. Chem. Lett. 13 (2005) 3385-3395
61. +, 45), 136 (23), 105 (100), 77 (73), 51 (23).