Abstract

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click reaction to efficient, practical and column-free preparation of the title compounds. The utility of the resulting unnatural amino acids as building blocks to prepare triazole possessing peptidomimetics is also delineated.

Keywords: Nα-Boc-bromomethylketones, one-pot click chemistry, CuI, N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole, N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole amino acids, amino acids, peptidomimetics, nanotubes, halides, dimethylacetylenedicarboxylate, triazole