Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl) phosphorimidate by reaction with aryl isocyanates

A Taher, S Eishenseher, Alexandra Martha Zoya Slawin, G Tennant, GW Weaver

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10 Citations (Scopus)

Abstract

The synthesis of a series of 2-aryl-2H, 4H-imidazo[4,5-d][ 1,2,3] triazoles is reported. These compounds are obtained in moderate to good yields by reaction of triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl) phosphorimidate with aryl isocyanates. The X-ray crystal structures of triethyl (N-1-methyl-4-nitro-1H-imidazol-5-yl) phosphorimidate and a 2-(4-trifluoromethylphenyl) substituted 2H, 4H-imidazo[4,5-d][1,2,3] triazole are reported. Spectroscopic evidence is provided for a carbodiimide intermediate proposed in the reaction mechanism.

Original languageEnglish
Pages (from-to)1968-1972
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
DOIs
Publication statusPublished - 2002

Keywords

  • CONJUGATED CARBODIIMIDES
  • DERIVATIVES
  • RING
  • IMINOPHOSPHORANES

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