‘Click Synthesis’ of 1<i>H</i>‐1,2,3‐Triazolyl‐Based Oxiconazole (=(1<i>Z</i>)‐1‐(2,4‐Dichlorophenyl)‐2‐(1<i>H</i>‐imidazol‐1‐yl)ethanone <i>O</i>‐[(2,4‐Dichlorophenyl)methyl]oxime) Analogs

Abstract

Abstract The ‘click synthesis’ of some oxiconazole analogs 5a – 5v having 1 H ‐1,2,3‐triazolyl residues by Huisgen cycloaddition was achieved in four steps ( Scheme 1 ). Oximation of phenacyl chloride ( 1 ) followed by azidation of 2‐chloro‐1‐phenylethanone oxime ( 2 ) provided azido ketoxime 3 . The CuI‐catalyzed Huisgen cycloaddition of 3 with terminal alkynes gave the 4‐substituted (at the triazole) 2‐(1 H ‐1,2,3‐triazol‐1‐yl)‐1‐phenylethanone oximes 4a – 4i . The O ‐alkylation of 4a – 4i with various alkyl halides resulted in the formation of the target molecules 5a – 5v in good yields.