Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed cross-coupling reactions

被引:42
作者
Conreaux, David
Bossharth, Emmanuel
Monteiro, Nuno
Desbordes, Philippe
Vors, Jean-Pierre
Balme, Genevieve
机构
[1] Univ Lyon 1, Lab Synthese Organometall & Mol Bioact, CNRS, UMR 5181,ESCPE, F-69622 Villeurbanne, France
[2] Bayer CropSci, F-69623 Lyon 09, France
关键词
D O I
10.1021/ol062721u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,5-Dihalogeno-4-methoxy-N-methylpyridin-2(1H)-ones have been shown to undergo single Suzuki coupling reactions in a site-selective fashion. Monoarylations occur at the C-5 position preferentially, thus leaving the remaining C-3 halide free for further functionalization, to finally access differentially 3,5-disubstituted 2-pyridones. This two-step strategy has been applied to the elaboration of the 3-acyl-5-aryl-4-oxy-2-pyridone subunit that is prevalent in numerous bioactive natural products.
引用
收藏
页码:271 / 274
页数:4
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