Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed cross-coupling reactions.
Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed cross-coupling reactions.
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DOI：
10.1002/chin.200720128
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发表时间：
2007-01
期刊：
影响因子：
5.2
通讯作者：
D. Conreaux;E. Bossharth;N. Monteiro;P. Desbordes;J. Vors;G. Balme*
中科院分区：
文献类型：
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作者：
D. Conreaux;E. Bossharth;N. Monteiro;P. Desbordes;J. Vors;G. Balme*
3，5-二卤代-4-甲氧基-N-甲基吡啶-2（1H）-酮已被证明以位点选择性方式进行单一Suzuki偶联反应。单芳基化优先发生在C-5位，从而使剩余的C-3卤化物游离用于进一步官能化，以最终获得差异化的3，5-二取代的2-吡啶酮。这种两步策略已被应用于3-酰基-5-芳基-4-氧-2-吡啶酮亚基的制备，该亚基在许多生物活性天然产物中普遍存在。[反应：见正文]。
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. [reaction: see text].