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A Dramatic Substituent Effect in Silver(I)‐Catalyzed Regioselective Cyclization of ortho ‐Alkynylaryl Aldehyde Oxime Derivatives
Author(s) -
Gao Hongyin,
Zhang Junliang
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800568
Subject(s) - chemistry , substituent , aldehyde , regioselectivity , oxime , catalysis , medicinal chemistry , dimethylacetamide , dimethylformamide , alkyl , selectivity , organic chemistry , solvent
A dramatic substituent effect was found in the silver(I)‐catalyzed cyclization reaction of ortho ‐alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)‐catalyzed reaction in dimethylacetamide at 110 °C (conditions A) affords isoquinolines in good to excellent yields, in contrast, isoquinolin‐1(2 H )‐ones were produced in moderate to high yields under conditions B (dimethylformamide, room temperature) when R is an acetyl group. A plausible mechanism was proposed for this product selectivity control reaction (PSCR) by subtle structure modification.