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‘Click Synthesis’ of 1 H ‐1,2,3‐Triazolyl‐Based Oxiconazole (=(1 Z )‐1‐(2,4‐Dichlorophenyl)‐2‐(1 H ‐imidazol‐1‐yl)ethanone O ‐[(2,4‐Dichlorophenyl)methyl]oxime) Analogs
Author(s) -
Soltani Rad Mohammad Navid,
Asrari Zeinab,
Behrouz Somayeh,
Hakimelahi Gholam Hossein,
KhalafiNezhad Ali
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100189
Subject(s) - chemistry , cycloaddition , oxime , click chemistry , alkyl , halide , chloride , medicinal chemistry , alkylation , triazole , combinatorial chemistry , phenacyl , catalysis , organic chemistry
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.