Synthesis And Variable Temperature Nmr Study Of Glucose Based 1,2,3-Triazole

In the current work, aromatic azide has been synthesized in one step from anthranilic acid. Then, the commercially available D-glucose has been utilized to prepare alkynyl glucose derivative in two subsequent steps from D-glucose. The cycloaddition reaction between the azide and terminal alkyne using click conditions afforded the glucose based 1,2,3-triazole in a moderate yield. The formation of all compounds is confirmed by 1D and 2D NMR spectra alongside with HRMS data. Moreover, variable temperature proton NMR VT-H-1 NMR experiments at four degrees (25, 35, 45 and 55 degrees C) are carried out for the resulting triazole and it is shown that there is significant shift in some of signals particularly the proton of the triazole ring and there is a broadening in the carboxyl proton signal.