4-(p-Chloro)phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the oxidation of 1,3,5-trisubstituted pyrazolines under mild conditions

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 833-836

  Zolfigol, Mohammad Ali ^a   Azarifar, Davood ^a   Mallakpour, Shadpour ^b   Mohammadpoor Baltork, Iraj ^c   Forghaniha, Ali ^a   Maleki, Behrooz ^a   Abdollahi Alibeik, Mohammad ^c  

^a BU ALI SINA UNIVERSITY   (Iran)

^b ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^c UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

1,3,5 Trisubstituted pyrazolines; 2 Imidazolines; 4 (p Chloro)phenyl 1,3,4 triazole 3,5 dione; 4 Substituted 1,3,4 triazole 3,5 dione; Aromatization; Imidazoles; Oxidation; Pyrazoles; Triazolinediones; Urazoles

Indexed keywords

OXIDIZING AGENT; PYRAZOLE DERIVATIVE; PYRAZOLINE DERIVATIVE; REAGENT; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 29544447714     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.088     Document Type: Article

References (45)

1. N. Nakamichi, Y. Kawashita, and M. Hayashi Synthesis 2004 1015
2. T.L. Gilchrist Heterocyclic Chemistry 2nd ed. 1992 John Wiley & Sons New York p 294
3. X.C. Gao, H. Cao, L.Q. Zhang, B.W. Zhang, Y. Cao, and C.H. Huang J. Mater. Chem. 9 1999 1077 1080
4. R.M. Claramunt, C. Lopez, M.D.L.A. Garcia, M. Pierrot, M. Giorgi, and J. Elguero J. Chem. Soc., Perkin Trans. 2 2000 2049 2053
5. J.A. Froggett, M.H. Hockley, and R.B. Titman J. Chem. Res. (S) 1997 30 31
6. J.E. Baldwin, G.J. Pritchard, and R.E. Rathmell J. Chem. Soc., Perkin Trans. 1 2001 2906 2908
7. S.A. Voznesenskii, L.I. Belen'kii, A.A. Dudinov, M.I. Struchkova, and M.M. Krayushkin Mendeleev Commun. 1998 1 42
8. A.C. Donohue, S. Pallich, and T.D. McCarthy J. Chem. Soc., Perkin Trans. 1 2001 1817 2822
9. G.H. Elgemeie, and N.H. Matwally J. Chem. Res. (S) 1999 384 385
10. K.T. Chang, Y.H. Choi, S.H. Kim, Y.J. Yoon, and W.S. Lee J. Chem. Soc., Perkin Trans. 1 2002 207 210
11. N. Nakamichi, Y. Kawashita, and M. Hayashi Org. Lett. 4 2002 3955 3957
12. J.N. Shah, and C.K. Shah J. Org. Chem. 43 1978 1266 1267
13. W.A.F. Goldstone, and R.O.C. Norman J. Chem. Soc., Chem. Commun. 1966 1536 1540
14. K. Auwers, and P. Heimke Liebigs Ann. 458 1927 186 220
15. I.G. Bhatnagar, and M.V. George Tetrahedron 24 1968 1293 1298
16. L.I. Smith, and K.L. Howard J. Am. Chem. Soc. 65 1943 159 164
17. R.P. Dodwadmath, and T.S. Wheeler Proc. Ind. Acad. Sci. 2A 1935 438 451
18. S.P. Singh, D. Kumar, O. Prakash, and R.P. Kapoor Synth. Commun. 27 1997 2683 2689
19. G. Sabitha, G.S.K. Kumar Reddy, Ch.S. Reddy, N. Fatima, and J.S. Yadav Synthesis 2003 1267 1271
20. R.S. Varma Green Chem. 1 1999 43 55
21. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025 1074
22. V. Krchnak, and M.W. Holladay Chem. Rev. 102 2002 61 91
23. S.E. Mallakpour, and M.A. Zolfigol Indian J. Chem. 34B 1995 183 and references cited therein
24. S.E. Mallakpour, and M.A. Zolfigol Indian J. Chem. 34B 1995 302
25. S.E. Mallakpour, and M.A. Zolfigol Indian J. Chem. 37B 1998 1001
26. S.E. Mallakpour, and M.A. Zolfigol Indian J. Chem. 38B 1999 777
27. M.A. Zolfigol, G. Chehardoli, and S.E. Mallakpour Synth. Commun. 33 2003 833
28. M.A. Zolfigol, H. Nasr-Isfahani, S.E. Mallakpour, and M. Safaiee Synlett 2005 761 and our references cited therein
29. M.A. Zolfigol, A. Ghorbani Choghamarani, M. Shahamirian, M. Safaiee, I. Mohammadpoor-Baltork, S. Mallakpour, and M. Abdollahi-Alibeik Tetrahedron Lett. 46 2005 5581
30. M.A. Zolfigol, D. Azarifar, and B. Maleki Tetrahedron Lett. 45 2004 2181
31. D. Azarifar, M.A. Zolfigol, and B. Maleki Bull. Korean Chem. Soc. 25 2004 23
32. D. Azarifar, M.A. Zolfigol, and B. Maleki Synthesis 2004 1744
33. I. Mohammadpoor-Baltork, M.A. Zolfigol, and M. Abdollahi-Alibeik Synlett 2004 2803
34. I. Mohammadpoor-Baltork, M.A. Zolfigol, and M. Abdollahi-Alibeik Tetrahedron Lett. 45 2004 8687
35. M. Abdollahi-Alibeik, I. Mohammadpoor-Baltork, and M.A. Zolfigol Bioorg. Med. Chem. Lett. 14 2004 6079
36. 18 were synthesized according to our previously reported procedure.
37. 3, 90 MHz): δ 6.86 (1H, S, CH), 7.32 (10H, m, Ar), 7.96 (5H, m, Ar).
38. M.A. Zolfigol, M.H. Zebarjadian, G. Chehardoli, S.E. Mallakpour, and M. Shamsipur Tetrahedron 57 2001 1627
39. M.A. Zolfigol, G.A. Chehardoli, and S.E. Mallakpour Synth. Commun. 33 2003 833
40. M.A. Zolfigol, S.E. Mallakpour, E. Madrakian, and E. Ghaemi Indian J. Chem. 39B 2000 308
41. M.A. Zolfigol, G.A. Chehardoli, S.E. Mallakpour, and H. Nasr-Isfahani Synth. Commun. 31 2001 1965
42. M.A. Zolfigol, M. Torabi, and S.E. Mallakpour Tetrahedron 57 2001 8381 and our other references cited therein
43. M.A. Zolfigol, M. Bagherzadeh, G.A. Chehardoli, S.E. Mallakpour, and M. Mamaghani J. Chem. Res. (S) 2001 390
44. M.A. Zolfigol, P. Salehi, S.E. Mallakpour, and M. Torabi Bull. Chem. Soc. Jpn. 76 2003 1673
45. D. Azarifar, and M. Shaebanzadeh Molecules 7 2002 885