Simple, Convenient and Heterogeneous Method for Conversion of Urazoles to Triazolinediones Using N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide or Trichloromelamine under Mild and Heterogeneous Conditions

Mohammad Ali Zolfigol; Ramin Ghorbani-Vaghei; Shadpour Mallakpour; Gholamabbas Chehardoli; Arash Ghorbani Choghamarani; Amaneh Hosain Yazdi

doi:10.1055/s-2006-926446

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Synthesis 2006(10): 1631-1634
DOI: 10.1055/s-2006-926446

PAPER

Simple, Convenient and Heterogeneous Method for Conversion of Urazoles to Triazolinediones Using N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide or Trichloromelamine under Mild and Heterogeneous Conditions

Mohammad Ali Zolfigol*^a, Ramin Ghorbani-Vaghei^a, Shadpour Mallakpour^b, Gholamabbas Chehardoli^a, Arash Ghorbani Choghamarani^a, Amaneh Hosain Yazdi^a
^a Department of Chemistry, College of Science, Bu-Ali Sina University, P. O. Box 4135, Hamadan 65174, Iran
e-Mail: Zolfi@basu.ac.ir;
^b Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran

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Publication History

Received 12 December 2005
Publication Date:
21 April 2006 (online)

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Abstract

N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide (TBBDA) or trichloromelamine (TCM) 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 excellent yields.

Key words

N,N,N′,N′-tetrabromobenzene-1,3-disulfonylamide - trichloromelamine - urazoles - bisurazoles - triazolinediones

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21

These compounds are sensitive to light, heat, alcohols, ethers, transition metals, and any nucleophiles. Also, they are very volatile - if the temperature rises over 50 °C in the course of removing of CH₂Cl₂, some TADs are removed with the solvent simultaneously. Therefore, the temperature must be controlled and CH₂Cl₂ is the best solvent for this purpose.