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N-Bromo Reagent Mediated Oxidation of Urazoles to Their Corresponding Triazolinediones under Mild and Heterogeneous Conditions

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Summary.

Various N-bromo reagents [HMTAB, DABCO-bromine, DPTBE, and TBCA] were used as effective oxidizing agents for the oxidation of urazoles and bisurazoles to their corresponding triazolinediones under mild and heterogeneous conditions at room temperature with good to excellent yields. Also the oxidation of some new 4-phenylurazole derivatives with these reagents is discussed.

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References

  • Chehardoli G (2006) Synlett: 2154 and references cited therein

  • SE Mallakpour GB Butler H Aghabozorg GJ Palenik (1985) Macromolecules 18 342 Occurrence Handle10.1021/ma00145a007 Occurrence Handle1:CAS:528:DyaL2MXhtFCiu7w%3D

    Article  CAS  Google Scholar 

  • MA Zolfigol AG Choghamarani M Shahamirian M Safaiee I Mohammadpoor-Baltork SE Mallakpour M Abdollahi-Alibeik (2005) Tetrahedron Lett 46 5581 Occurrence Handle10.1016/j.tetlet.2005.06.031 Occurrence Handle1:CAS:528:DC%2BD2MXmtFCksrg%3D

    Article  CAS  Google Scholar 

  • MA Zolfigol D Azarifar SE Mallakpour I Mohammadpoor-Baltork A Forghaniha B Maleki M Abdollahi-Alibeik (2006) Tetrahedron Lett 47 833 Occurrence Handle10.1016/j.tetlet.2005.11.088 Occurrence Handle1:CAS:528:DC%2BD2MXhtlCiu7rO

    Article  CAS  Google Scholar 

  • A Christoforou G Nicolaou Y Elemes (2006) Tetrahedron Lett 47 9211 Occurrence Handle10.1016/j.tetlet.2006.10.134 Occurrence Handle1:CAS:528:DC%2BD28Xht1KktbrL

    Article  CAS  Google Scholar 

  • JC Stickler WH Pirkle (1966) J Org Chem 31 3444 Occurrence Handle10.1021/jo01348a532 Occurrence Handle1:CAS:528:DyaF2sXjslygtQ%3D%3D

    Article  CAS  Google Scholar 

  • Read G, Richardson NR (1996) J Chem Soc Perkin Trans 1: 167

    Google Scholar 

  • VP Arya S Shenoy (1976) Indian J Chem 14B 883 Occurrence Handle1:CAS:528:DyaE2sXktl2gtbk%3D

    CAS  Google Scholar 

  • H Warnho K Wald (1975) Org Prep Proced Int 7 251 Occurrence Handle10.1080/00304947509355156

    Article  Google Scholar 

  • SE Mallakpour (1992) J Chem Ed 69 238 Occurrence Handle1:CAS:528:DyaK38XitFeltbk%3D Occurrence Handle10.1021/ed069p238

    Article  CAS  Google Scholar 

  • SE Mallakpour MA Zolfigol (1993) J Sci I R Iran 4 199 Occurrence Handle1:CAS:528:DyaK2MXjsFWqsb8%3D

    CAS  Google Scholar 

  • MA Zolfigol M Bagherzadeh SE Mallakpour G Chehardoli AG Choghamarani E Kolvari N Koukabi (2007) Catal Commun 8 256 Occurrence Handle10.1016/j.catcom.2006.04.006 Occurrence Handle1:CAS:528:DC%2BD28Xht1ykt7nM

    Article  CAS  Google Scholar 

  • A Bamoniri MA Zolfigol I Mohammadpoor-Baltork BF Mirjalili (2006) J Iran Chem Soc 3 85 Occurrence Handle1:CAS:528:DC%2BD28XivVWhsrw%3D

    CAS  Google Scholar 

  • K Niknam MA Zolfigol (2006) J Iran Chem Soc 3 59 Occurrence Handle1:CAS:528:DC%2BD28XivVWiu7k%3D

    CAS  Google Scholar 

  • H Firouzabadi AA Jafari (2005) J Iran Chem Soc 2 85 Occurrence Handle1:CAS:528:DC%2BD2MXmtVOgur8%3D

    CAS  Google Scholar 

  • K Niknam MA Zolfigol T Sadabadi A Nejati (2006) J Iran Chem Soc 3 318 Occurrence Handle1:CAS:528:DC%2BD2sXhtVCksQ%3D%3D

    CAS  Google Scholar 

  • MA Zolfigol M Bagherzadeh K Niknam F Shirini I Mohammadpoor-Baltork AG Choghamarani M Baghbanzadeh (2006) J Iran Chem Soc 3 73 Occurrence Handle1:CAS:528:DC%2BD28XivVWhsr4%3D

    CAS  Google Scholar 

  • P Salehi MA Zolfigol F Shirini M Baghbanzadeh (2006) Curr Org Chem 10 2171 Occurrence Handle10.2174/138527206778742650 Occurrence Handle1:CAS:528:DC%2BD28XhtFemsrbI

    Article  CAS  Google Scholar 

  • Yavari I, Shaabani A (1994) J Chem Res (S) 274

  • MM Heravi F Derikvand M Ghassemzadeh B Neumuller (2005) Tetrahedron Lett 46 6243 Occurrence Handle10.1016/j.tetlet.2005.07.057 Occurrence Handle1:CAS:528:DC%2BD2MXns1Sgsr4%3D

    Article  CAS  Google Scholar 

  • V Kavala S Naik BK Patel (2005) J Org Chem 70 4267 Occurrence Handle10.1021/jo050059u Occurrence Handle1:CAS:528:DC%2BD2MXjsVGgtrg%3D

    Article  CAS  Google Scholar 

  • MM Heravi D Ajami MA Nooshabadi (1999) Iran J Chem Eng 18 88 Occurrence Handle1:CAS:528:DC%2BD3cXltVegtL4%3D

    CAS  Google Scholar 

  • Beheshtiha YS, Heravi MM, Sarmad N, Shoar RH (2001) J Chem Res (S) 76

  • MA Nooshabadi K Aghapoor M Tajbakhsh MM Heravi (2001) J Sci I R Iran 12 1

    Google Scholar 

  • MB Dehkordi MM Heravi P Khosrofar A Ziafati M Ghassemzadeh (2004) Phosphorus Sulfur Silicon 179 2595 Occurrence Handle10.1080/10426500490494697 Occurrence Handle1:CAS:528:DC%2BD2MXisF2rug%3D%3D

    Article  CAS  Google Scholar 

  • MB Dehkordi MM Heravi A Ziafati P Khosrofar M Ghassemzadeh (2004) Phosphorus Sulfur Silicon 179 1493 Occurrence Handle10.1080/10426500490463952 Occurrence Handle1:CAS:528:DC%2BD2cXnt1WitLc%3D

    Article  CAS  Google Scholar 

  • M Heravi F Derikvand M Ghassemzadeh (2006) Synthetic Commun 36 581 Occurrence Handle10.1080/00397910500406476 Occurrence Handle1:CAS:528:DC%2BD28XhsVSlsrs%3D

    Article  CAS  Google Scholar 

  • Bandegar BP, Admane SB, Jare SS (1998) J Chem Res (S) 154

  • a) De Almeida LS, Esteves PM, De Mattos MCS (2006) Synthesis 221; b) De Almeida LS, Esteves PM, De Mattos MCS (2006) Synlett: 1515

  • Zolfigol MA, Ghorbani-Vaghei R, Mallakpour SE, Chehardoli GA, Choghamarani AG, Yazdi HA (2006) Synthesis 1631

  • MA Zolfigol E Ghaemi E Madrakian AG Choghamrani (2006) Mendeleev Commun 1 41 Occurrence Handle10.1070/MC2006v016n01ABEH002116 Occurrence Handle1:CAS:528:DC%2BD28XisFKqurY%3D

    Article  CAS  Google Scholar 

  • Zolfigol MA, Shirini F, Choghamarani AG (2006) Synthesis: 2043

  • MA Zolfigol A Khazaei AG Choghamarani A Rostami M Hajjami (2006) Catal Commun 7 399 Occurrence Handle10.1016/j.catcom.2005.12.004 Occurrence Handle1:CAS:528:DC%2BD28XjvFymtbs%3D

    Article  CAS  Google Scholar 

  • Zolfigol MA, Madrakian E, Ghaemi E (2003) Synlett: 2222

  • Zolfigol MA, Madrakian E, Ghaemi E (2003) Synlett: 191

  • Zolfigol MA, Bagherzadeh M, Chehardoli G, Mallakpour SE, Mamaghani M (2001) J Chem Res (S) 390

  • Zolfigol MA, Nassr-Isfahani H, Mallakpour SE, Safaiee M (2005) Synlett: 761

  • Azarifar D, Zolfigol MA, Maleki B (2004) Synthesis: 1744

  • D Azarifar MA Zolfigol B Maleki (2004) Tetrahedron Lett 45 2181 Occurrence Handle10.1016/j.tetlet.2004.01.038 Occurrence Handle1:CAS:528:DC%2BD2cXhtlOqtro%3D

    Article  CAS  Google Scholar 

  • E Kolvari A Ghorbani-Choghamarani P Salehi F Shirini MA Zolfigol (2007) J Iran Chem Soc 4 126 Occurrence Handle1:CAS:528:DC%2BD2sXntVyhs7c%3D

    CAS  Google Scholar 

  • Figueira VBC (2006) Synlett: 2681 and references cited therein

Download references

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Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran

    Mohammad Ali Zolfigol, Gholamabbas Chehardoli, Ezat Ghaemi, Elaheh Madrakian, Reza Zare & Tahereh Azadbakht

  2. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, Iran

    Khodabakhsh Niknam

  3. Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, Iran

    Shadpour Mallakpour

Authors
  1. Mohammad Ali Zolfigol
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  2. Gholamabbas Chehardoli
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  3. Ezat Ghaemi
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  4. Elaheh Madrakian
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  5. Reza Zare
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  6. Tahereh Azadbakht
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  7. Khodabakhsh Niknam
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  8. Shadpour Mallakpour
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Corresponding authors

Correspondence to Mohammad Ali Zolfigol or Gholamabbas Chehardoli.

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Zolfigol, M., Chehardoli, G., Ghaemi, E. et al. N-Bromo Reagent Mediated Oxidation of Urazoles to Their Corresponding Triazolinediones under Mild and Heterogeneous Conditions. Monatsh Chem 139, 261–265 (2008). https://doi.org/10.1007/s00706-007-0785-0

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  • DOI: https://doi.org/10.1007/s00706-007-0785-0

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