Synthesis and Characterization of Benzimidazolium Salts Bearing Triazole Groups

Abstract

A propargyl-functionalized salt, 1-(2-methoxyethyl)-3-(prop-2-ynyl)benzimidazolium bromide (1), was prepared. 1-(2-methoxyethyl)-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]benzimidazolium hexafluorophos- phate (2) and 1-(2-methoxyethyl)-3-[(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl]benzimidazolium hexafluorophosphate (3) were obtained by Cu(I) catalyzed azide-alkyne cycloaddition reaction of 1 with corresponding azides. Compound 3 was transformed to 1-(2-methoxyethyl)-3-[(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)methyl]benzimidazolium hexafluorophosphate (4) by reduction reaction with hydrazine monohydrate. The structures of these  propargyl- and 1,2,3-triazolyl-functionalized benzimidazolium salts were elucidated by FT-IR, ¹H NMR, ¹³C NMR and elemental analysis methods.

Keywords

• Benzimidazolium,N-heterocyclic carbene,Click chemistry,triazole

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