Iodogen: A novel reagent for the oxidation of urazoles under heterogeneous conditions

Synthesis

Volumn , Issue 16, 2009, Pages 2729-2732

  Khoramabadi Zad, Ahmad ^a,b   Shiri, Azam ^a   Zolfigol, Mohammad Ali ^a   Mallakpour, Shadpour ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

^b ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Chloroamides; Glycolurils; Iodogen; Oxidations

Indexed keywords

CHLOROAMIDES; GLYCOLURILS; HETEROGENEOUS CONDITIONS; IODOGEN; OXIDIZING AGENTS; ROOM TEMPERATURE;

OXIDATION;

4 (4 CHLOROPHENYL) 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 (4 METHOXYPHENYL) 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 (4 NITROPHENYL) 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 (4 TERT BUTYLPHENYL) 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 ETHYL 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 METHYL 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4 PHENYL 3H 1,2,4 TRIAZOLE 3,5 DIONE; 4,4' HEXANE 1,6 DIYLBIS(3H 1,2,4 TRIAZOLE 3,5 DIONE); IODOGEN; OXIDIZING AGENT; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; URAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; ROOM TEMPERATURE;

EID: 70449411289     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216902     Document Type: Article

References (46)

1. Fraker, P. J.; Speck, J. C. Jr. Biochem. Biophys. Res. Commun. 1978, 80, 849.
2. Weinmann, H.; Tilstam, U. Org. Process Res. Dev. 2002, 6, 384.
3. Kolvari, E.; Ghorbani-Choghamarani, A.; Salehi, P.; Shirini, F.; Zolfigol, M. A. J. Iran Chem. Soc. 2007, 4, 126.
4. Hiegel, G. A.; Hogenauer, T. J.; Lewis, J. C. Synth. Commun. 2005, 35, 2099.
5. Luca, L. D.; Giacomelli, G. Synlett 2004, 2180.
6. Biltz, H.; Behrens, O. Chem. Ber. 1910, 43, 1984.
7. Williams, J. W. US Patent 2,649,389, 1953;
8. Chem. Abstr. 1953, 48, 8267.
9. Adkins, H. B. US Patent 2,654,763, 1953;
10. Chem. Abstr. 1953, 48, 10778.
11. Slezak, F. B.; Hirsch, A.; Rosen, I. J. Org. Chem. 1960, 25, 660.
12. Slezak, F. B.; Bluestone, H.; Magee, T. A.; Wotiz, J. H. J. Org. Chem. 1962, 27, 2181.
13. Zettler, T. T. US Patent 3,252,901, 1966;
14. Chem. Abstr. 1966, 65, 6922.
15. Horvath, R. J.; Parsons, C. G.; Zettler, T. T. US Patent 3,445,383, 1969;
16. Chem. Abstr. 1969, 70, 109008.
17. Unak, T.; Akgun, Z.; Yildirim, Y.; Dumanb, Y.; Erenel, G. Appl. Radiat. Isot. 2001, 54, 749.
18. Yuan, H.; Luo, J.; Field, S.; Weissleder, R.; Cantley, L.; Josephson, L. Bioconjugate Chem. 2005, 16, 669.
19. Safavy, A.; Georg, G. I.; Velde, D. V.; Raisch, K. P.; Safavy, K.; Carpenter, M.; Wang, W.; Bonner, J. A.; Khazaeli, M. B.; Buchsbaum, D. J. Bioconjugate Chem. 2004, 15, 1264.
20. Cook, J.; Pratt, R.; Lilien, J. Biochemistry 1984, 23, 899.
21. Borhani, D. W.; Greene, F. D. J. Org. Chem. 1986, 51, 1563.
22. Pirkle, W. H.; Stickler, J. C. J. Am. Chem. Soc. 1970, 92, 7497.
23. Alstanei, A.-M.; Hornoiu, C.; Aycard, J.-P.; Carles, M.; Volanschi, E. J. Electroanal. Chem. 2003, 542, 13; and references therein.
24. Hall, J. H.; Krishnan, G. J. Org. Chem. 1984, 49, 2498.
25. Hall, J. H.; Jones, M. L. J. Org. Chem. 1983, 48, 822.
26. Seymour, G. A.; Green, F. D. J. Am. Chem. Soc. 1980, 102, 6384.
27. Mallakpour, S. E.; Butler, G. B. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 217.
28. Mallakpour, S. E.; Butler, G. B. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 125.
29. Mallakpour, S. E.; Butler, G. B. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 2781.
30. Klindert, T.; Seitz, G. Synth. Commun. 1996, 26, 2587.
31. Wilson, R. M.; Chantarasiri, N. J. Am. Chem. Soc. 1991, 113, 2301.
32. Cookson, R. C.; Stevens, I. D. R.; Watts, C. T. Chem. Commun. 1966, 744.
33. Mallakpour, S. E.; Butler, G. B.; Aghabozorg, H.; Palenik, G. J. Macromolecules 1985, 18, 342.
34. Read, G.; Richardson, N. R. J. Chem. Soc., Perkin Trans. 1 1996, 167.
35. Arya, V. P.; Shenoy, S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14, 883.
36. Warnho, H.; Wald, K. Org. Prep. Proced. Int. 1975, 7, 251.
37. Mallakpour, S. E. J. Chem. Educ. 1992, 69, 238.
38. Mallakpour, S. E.; Zolfigol, M. A. J. Sci. I. R. Iran 1993, 4, 199.
39. Zolfigol, M. A.; Gorbani-Vaghei, R.; Mallakpour, S.; Chehardoli, G.; Ghorbani Choghamarani, A.; Hosein Yazdi, A. Synthesis 2006, 1631.
40. Zolfigol, M. A.; Nasr-Isfahani, H.; Mallakpour, S.; Safaiee, M. Synlett 2005, 761.
41. Zolfigol, M. A.; Madrakian, E.; Ghaemi, E.; Mallakpour, 5.
42. Synlett 2002, 1633.
43. Zolfigol, M. A.; Bagherzadeh, M.; Chehardoli, G.; Mallakpour, S.; Mamaghani, M. J. Chem. Res. 2001, 390.
44. Khoramabadi A., Shiri A. unpublished results.
45. Zolfigol, M. A.; Chehardoli, G.; Ghaemi, E.; Madrakian, E.; Zare, R.; Azadbakht, T.; Niknam, K.; Mallakpour, S. Monatsh. Chem. 2008, 139, 261.
46. As the product 4-substituted-3H-1,2,4-triazole-3,5-diones are very volatile, it is important that the temperature be maintained below 50 °C during evaporation of the solvent to prevent loss of material.