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The synthesis began by chemoselective reduction of dimethyl 3-oxo-glutarate 1 using NaBH4 and citric acid to afford dimethyl 3-hydroxy-glutarate 2. The sequence of preparation required protection of secondary alcohol and reduction of esters moieties, performed with DHP on acid catalysis (PTSA) followed by treatment of crude with LiAlH4 in THF, respectively. The symmetrical diol 3, obtained in 50% for two steps, was monoprotected with TBSCl, leading to the alcohol 4. The next stage was the hydroxyl protection with TsCl in the presence of DMAP and Et3N in DCM, leading to the formation of fully protected 5. Azido treatment in hot acetonitrile yielded 6. The cycloaddition of azide compound 6 with hept-1-yno in heterogeneous mixture of DCM and water with use of CuSO4 as catalyst produced the alcohol-triazole 7 in 33%.

Synthesis of Triazoles with Potential Antileishmanial Activity by Click Chemistry