A hydrazone ligand, (E)-6-(2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinyl)nicotinohydrazide
(H2L), was synthesized and characterized by spectroscopic
methods. The reaction of H2L with CuCl2·2H2O in methanol gave Cu(II) coordination compound, [Cu(HL′)(Cl)]·CH3OH (1), which was characterized by elemental
analysis and spectroscopic methods (Fourier transform infrared (FT-IR)
and UV–vis). The structure of 1 was also determined
by single-crystal X-ray analysis. Structural studies confirmed the
formation of esteric group during the synthesis of 1.
Compound 1 was immobilized on 3-aminopropyltriethoxysilane
(APTS)-functionalized silica gel through the amidification reaction
and the obtained heterogeneous coordination compound was utilized
as a catalyst for the three-component azide–epoxide–alkyne
cycloaddition reaction in water as a green solvent. The structural
properties of the heterogeneous catalyst were characterized by a combination
of FT-IR, UV–vis, thermogravimetric analysis (TGA), scanning
electron microscopy (SEM) and energy-dispersive spectrometry (EDS)
analyses. The effect of the amount of catalyst and temperature on
the cycloaddition reaction was studied, and the obtained 1,2,3-triazoles
were characterized by spectroscopic studies and single-crystal X-ray
analysis. The catalytic investigations revealed that this catalytic
system has high activity in the synthesis of β-hydroxy-1,2,3-triazoles.
It was also found that the aromatic and aliphatic substituents on
the alkyne and epoxide together with the reaction temperature have
considerable effects on the activity and regioselectivity of this
catalytic system.