Synthesis studies toward chloroazaphilone and vinylogous γ-pyridones:: Two common natural product core structures
Synthesis studies toward chloroazaphilone and vinylogous γ-pyridones:: Two common natural product core structures
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DOI：
10.1021/jo050414g
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发表时间：
2005-06-10
影响因子：
3.6
通讯作者：
Yao, ZJ
中科院分区：
文献类型：
--
作者：
Wei, WG;Yao, ZJ
[图表]氯氮杂酮是许多天然产物中常见的结构。本文报道了一种模型氯氮杂酮的实际合成，该模型在关键的一锅操作中利用 HClO4/HOAc 吡啶鎓盐的 Pb(OAc)(4) 氧化。还充分研究了这种氯氮杂酮与各种伯胺的反应以提供相应的插烯γ-吡啶酮。稳定烯胺中间体的分离提供了反应机制的直接证据。
[GRAPHICS]Chloroazaphilone is a common structure found in a number of natural products. Reported herein is a practical synthesis of a model chloroazaphilone that utilizes Pb(OAc)(4) oxidation of HClO4/HOAc pyrinium salt in a key one-pot operation. Reaction of this chloroazaphilone with various primary amines to afford the corresponding vinylogous gamma-pyridones was also fully investigated. The isolation of stable enamine intermediates provided direct evidence of reaction mechanisms.