Click Synthesis' of 1H-1,2,3-Triazolyl-Based Oxiconazole (=(1Z)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone O-[(2,4-Dichlorophenyl)methyl]oxime) Analogs

The click synthesis of some oxiconazole analogs 5a5v having 1H-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-(1H-1,2,3-triazol-1-yl)-1-phenylethanone oximes 4a4i. The O-alkylation of 4a4i with various alkyl halides resulted in the formation of the target molecules 5a5v in good yields.