RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(16): 2729-2732
DOI: 10.1055/s-0029-1216902
DOI: 10.1055/s-0029-1216902
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Iodogen: A Novel Reagent for the Oxidation of Urazoles under Heterogeneous Conditions
Weitere Informationen
Received
9 April 2009
Publikationsdatum:
14. Juli 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. Juli 2009 (online)

Abstract
Iodogen is employed as an efficient oxidizing agent for the conversion of urazoles and bis-urazoles into the corresponding 1,2,4-triazoles in good to excellent yields under mild heterogeneous conditions at room temperature.
Key words
iodogen - oxidations - chloroamides - glycolurils
- 1
Fraker PJ.Speck JC. 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 MA. J. Iran Chem. Soc. 2007, 4: 126 - 4
Hiegel GA.Hogenauer TJ.Lewis JC. Synth. Commun. 2005, 35: 2099 - 5
Luca LD.Giacomelli G. Synlett 2004, 2180 - 6
Biltz H.Behrens O. Chem. Ber. 1910, 43: 1984 - 7
Williams JW. inventors; US Patent 2,649,389. ; Chem. Abstr. 1953, 48, 8267 - 8
Adkins HB. inventors; US Patent 2,654,763. ; Chem. Abstr. 1953, 48, 10778 - 9
Slezak FB.Hirsch A.Rosen I. J. Org. Chem. 1960, 25: 660 - 10
Slezak FB.Bluestone H.Magee TA.Wotiz JH. J. Org. Chem. 1962, 27: 2181 -
11a
Zettler TT. inventors; US Patent 3,252,901. ; Chem. Abstr. 1966 , 65, 6922 -
11b
Horvath RJ,Parsons CG, andZettler TT. inventors; US Patent 3,445,383. ; Chem. Abstr. 1969, 70, 109008 - 12
Unak T.Akgun Z.Yildirim Y.Dumanb Y.Erenel G. Appl. Radiat. Isot. 2001, 54: 749 - 13
Yuan H.Luo J.Field S.Weissleder R.Cantley L.Josephson L. Bioconjugate Chem. 2005, 16: 669 - 14
Safavy A.Georg GI.Velde DV.Raisch KP.Safavy K.Carpenter M.Wang W.Bonner JA.Khazaeli MB.Buchsbaum DJ. Bioconjugate Chem. 2004, 15: 1264 - 15
Cook J.Pratt R.Lilien J. Biochemistry 1984, 23: 899 - 16
Borhani DW.Greene FD. J. Org. Chem. 1986, 51: 1563 - 17
Pirkle WH.Stickler JC. J. Am. Chem. Soc. 1970, 92: 7497 - 18
Alstanei A.-M.Hornoiu C.Aycard J.-P.Carles M.Volanschi E. J. Electroanal. Chem. 2003, 542: 13 ; and references therein -
19a
Hall JH.Krishnan G. J. Org. Chem. 1984, 49: 2498 -
19b
Hall JH.Jones ML. J. Org. Chem. 1983, 48: 822 -
19c
Seymour GA.Green FD. J. Am. Chem. Soc. 1980, 102: 6384 -
20a
Mallakpour SE.Butler GB. J. Polym. Sci., Part A: Polym. Chem. 1989, 27: 217 -
20b
Mallakpour SE.Butler GB. J. Polym. Sci., Part A: Polym. Chem. 1989, 27: 125 -
20c
Mallakpour SE.Butler GB. J. Polym. Sci., Part A: Polym. Chem. 1987, 25: 2781 - 21
Klindert T.Seitz G. Synth. Commun. 1996, 26: 2587 - 22
Wilson RM.Chantarasiri N. J. Am. Chem. Soc. 1991, 113: 2301 - 23
Cookson RC.Stevens IDR.Watts CT. Chem. Commun. 1966, 744 - 24
Mallakpour SE.Butler GB.Aghabozorg H.Palenik GJ. Macromolecules 1985, 18: 342 -
25a
Read G.Richardson NR. J. Chem. Soc., Perkin Trans. 1 1996, 167 -
25b
Arya VP.Shenoy S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14: 883 -
25c
Warnho H.Wald K. Org. Prep. Proced. Int. 1975, 7: 251 -
25d
Mallakpour SE. J. Chem. Educ. 1992, 69: 238 -
25e
Mallakpour SE.Zolfigol MA. J. Sci. I. R. Iran 1993, 4: 199 -
26a
Zolfigol MA.Gorbani-Vaghei R.Mallakpour S.Chehardoli G.Ghorbani Choghamarani A.Hosein Yazdi A. Synthesis 2006, 1631 -
26b
Zolfigol MA.Nasr-Isfahani H.Mallakpour S.Safaiee M. Synlett 2005, 761 -
26c
Zolfigol MA.Madrakian E.Ghaemi E.Mallakpour S. Synlett 2002, 1633 -
26d
Zolfigol MA.Bagherzadeh M.Chehardoli G.Mallakpour S.Mamaghani M. J. Chem. Res. 2001, 390 - 28
Zolfigol MA.Chehardoli G.Ghaemi E.Madrakian E.Zare R.Azadbakht T.Niknam K.Mallakpour S. Monatsh. Chem. 2008, 139: 261
References
Khoramabadi A., Shiri A. unpublished results.
29As 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.