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‘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

✍ Scribed by Mohammad Navid Soltani Rad; Zeinab Asrari; Somayeh Behrouz; Gholam Hossein Hakimelahi; Ali Khalafi-Nezhad

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
256 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

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.

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