Several disubstituted 1H-1,2,3-triazoles have been prepared using the CuAAC method developed by Sharpless and Meldal. Trisubstituted triazoles have also been prepared using a symmetric internal alkyne for cycloaddition. The trisubstituted products were produced thermally without solvent or catalyst. The triazoles were synthesized in keeping with the “green” chemistry principles listed by the American Chemical Society. The triazoles were to be investigated for both their metal and enzyme binding capabilities. Different methods of alkyl azide preparation including microwave methods were investigated to determine the best procedure for azide synthesis. The 1H-1,2,3-triazoles synthesized included mono- and diesters and mono- and dicarboxylic acids. The triazole monoesters were prepared regioselectively utilizing the CuAAC method starting with organic azides and a terminal alkyne. Purification of the triazole esters and diesters was achieved in good yield without chromatographic separation. The purified triazole esters were hydrolyzed to form triazole carboxylic acids.

Synthesis of 1H-1,2,3-triazole esters and acids

249th National Meeting (2015)

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