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‘Click Synthesis’ of Some Novel O ‐Substituted Oximes Containing 1,2,3‐Triazole‐1,4‐diyl Residues as New Analogs of β ‐Adrenoceptor Antagonists
Author(s) -
Rad Mohammad Navid Soltani,
Behrouz Somayeh,
Karimitabar Fatemeh,
KhalafiNezhad Ali
Publication year - 2012
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.201100324
Subject(s) - chemistry , benzophenone , propargyl , propargyl bromide , cycloaddition , oxime , triazole , bromide , click chemistry , 1,2,3 triazole , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The ‘click synthesis’ of some novel O ‐substituted oximes, 7a – 7t , which contain 1,2,3‐triazolediyl residues, as new analogs of β ‐adrenoceptor antagonists is described ( Schemes 1 – 4 ). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9 H ‐fluoren‐9‐one and benzophenone, i.e. , 9a and 9b , respectively, followed by their reaction with propargyl bromide, afforded O ‐propargyl oximes 10a and 10b , respectively, which by a subsequent CuI‐catalyzed Huisgen cycloaddition with prepared β ‐azido alcohols 11a – 11j ( Schemes 2 and 3 ), led to the target compounds 7a – 7t in good yields.