A combination of inorganic hydrolysable chloride salts and UHP (hydrogen peroxide–urea complex) in the presence of wet SiO2 was used as an effective oxidising agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions in good to excellent yields. Oxidation of urazoles and bis-urazoles also occurred with N,N,2,3,4,5,6-heptachloroaniline. The in situ generation of Cl+ appears to be required for the oxidation of urazoles using these reagents.
(a) HallJ.H., and KrishnanG., J. Org. Chem., 1984, 49, 2498
7.
HallJ.H., and JonesM. L., J. Org. Chem., 1983, 48, 822
8.
SeymourG.A., and GreenF. D., J. Am. Chem. Soc., 1980, 102, 6384.
9.
MallakpourS.E., ButlerG. B., AghabozorgH., and PalanikG., J. Macromolecules, 1985, 18, 342
10.
LaiY.C., MallakpourS. E., ButlerG. B., and PalanikG., J. Org. Chem., 1985, 50, 4378.
11.
(a) MallakpourS.E., and ButlerG. B., J. Polym. Sci. Part A: Polym. Chem. Ed., 1989, 27, 217
12.
MallakpourS.E., and ButlerG. B., J. Polym. Sci. Part A: Polym. Chem. Ed., 1989, 27, 125
13.
MallakpourS.E., and ButlerG. B., J. Polym. Sci. Part A: Polym. Chem. Ed., 1987, 25, 2781.
14.
KlindertT., and SeitzG., Synth. Commun., 1996, 26, 2587. and references therein.
15.
(a) CooksonR.C., StevensI. D. R., and WattsC. T., Chem. Commun.1966, 744
16.
BorhaniD.W., and GreenF. D., J. Org. Chem., 1986, 51, 1563
17.
AkasakaT., SonobeH., SatoR., and AndoW., Tetrahedron Lett., 1984, 25, 4757.
18.
SticklerJ.C., and PirkleW. H., J. Org. Chem., 1966, 31, 3444.
19.
ReadG., and RechardsonN. R., J. Chem. Soc. Perkin Trans., 1, 1996, 167.
20.
MallakpourS.E., J. Chem. Ed., 1992, 69, 238.
21.
MallakpourS.E., and ZolfigolM. A., J. Sci. I. R. Iran, 1993, 4, 199.
22.
(a) ZolfigolM.A., Synth. Commun., 1999, 29, 905
23.
ZolfigolM.A., NematollahiD., and MallakpourS. E., Synth. Commun., 1999, 29, 2277
24.
ZolfigolM.A., and MallakpourS. E., Synth. Commun., 1999, 29, 4061
25.
ZolfigolM.A., Kiany-BorazjaniM., SadeghiM. M., Mohammadpoor-BaltorkI., and MemarianH. R., Synth. Commun., 2000, 30, 551
26.
ZolfigolM.A., GhaemiE., and MadrakianE., Synth. Commun., 2000, 30, 1989
27.
ZolfigolM.A., Synth. Commun., 2000, 30, 1593
28.
ZolfigolM.A., Kiany-BorazjaniM., MallakpourS. E., and Nasr-IsfahaniH., Synth. Commun., 2000, 30, 2573
29.
ZolfigolM.A., Kiany-BorazjaniM., SadeghiM. M., MemarianH. R., and Mohammadpoor-BaltorkI., J. Chem. Research(S), 2000, 167.
30.
ZolfigolM.A., MallakpourS. E., MadrakianE., and GhaemiE., Ind. J. Chem., 2000, 39B, 308
31.
ZolfigolM.A., GhaemiE., MadrakianE., and Kiany-BorazjaniM., Synth. Commun., 2000, 30, 2057
32.
ZolfigolM.A., Kiany-BorazjaniM., SadeghiM. M., MemarianH. R., and Mohammadpoor-BaltorkI., Synth. Commun., 2000, 30, 2945
33.
ZolfigolM.A., Kiany-BorazjaniM., SadeghiM. M., Mohammadpoor-BaltorkI., and MemarianH. R., Synth. Commun., 2000, 30, 3919
34.
ZolfigolM.A., ShiriniF., Ghorbani ChoghamaraniA., Taqian-nasabA., KeypourH., and SalehzadehS., J. Chem. Research(S), 2000, 420.
35.
CooperM.S., HeaneyH., NewboldA. J., and SandersonW. R., Synlett, 1990, 533.
36.
BalliniR., MarcantoniE., and PetriniM., Tetrahedron Lett., 1992, 33, 4835.
37.
AstodilloL., GalindoA., GonzalezA. G., and MansillaH., Heterocycles, 1993, 36, 1075.
38.
BalickiR., Synth. Commun., 1999, 29, 2235.
39.
VarmaR.S., and NaickerK. P., Org. Lett., 1999, 1, 189.
40.
CaronS., DoN. M., and SieserJ. E., Tetrahedron Lett., 2000, 41, 2299.
41.
(a) AryaV.P., and ShenoyS. J., Ind. J. Chem., 1976, 14B, 883
42.
BurrageM.E., CooksonR. C., GupteS. S., and StevensI. D. R., J. Chem. Soc. Perkin Trans. 1I, 1975, 1325.
43.
WamhoffH., and WaldK., Org. Prep. Proc. Int., 1975, 7, 251.
44.
MallakpourS. E., and ButlerG. B. in Advances in Polymer Synthesis, CulbertsonB. M., and McGrath, (eds) J.E. Polymer Science and Technology Series, Vol 31, Plenum, New York, 1985, pp. 1–25.
45.
(a) BanksR.E., BarlowM. G., HornbyJ. C., and MamaghaniM., J. Chem. Soc. Perkin Trans. 1, 1980, 817.
46.
MamaghaniM., and BanksR. E., J. Sci. I. R. Tran, 1994, 5, 98.
47.
GoldschmidtS., and StrohmengerL., Ber., 1922, 55, 2450.
48.
These compounds are sensitive to the light, heat, alcohols, ethers, transition metals and any nucleophiles. Also they are very volatile so that, if temperature rises over than 50 °C in the course of removing of CH2Cl2, some of TADs are simultaneously removed with solvent. Therefore, the temperature must be controlled and dichloromethane is the best solvent for this purpose.