Synthesis studies toward chloroazaphilone and vinylogous gamma-pyridones: two common natural product core structures |
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Authors: | Wei Wan-Guo Yao Zhu-Jun |
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Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. |
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Abstract: | 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. |
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