Synthesis of substituted 1,2-benzoquinones and substituted 3-hydroxy-4 (1H) -pyridinones: Application of oxidation-Michael addition in organic synthesis |
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| Authors: | LI Miao-Sheng MA Lin ZHANG Xiao-Chun HUANG Zhi-Shu XIAO Shao-Hua GU Lian-Quan |
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| Institution: | LI,Miao-Sheng MA,Lin ZHANG,Xiao-Chun HUANG,Zhi-Shu XIAO,Shao-Hua GU,Lian-Quan
Department of Chemistry,Zhongshan University,Guangzhou,Guangdong 510275,China |
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| Abstract: | Catechol (1) and 2-ethoxy-2-ethyl-3-hydroxy-4(1H)-pyridinone (4) derivatives can be oxidized to give ortho-quinone of 1,2-benzoquinone (2) and 2-ethoxy-2-ethyl-l,2(2H)-pyridine-3,4-dione (5) that subsequently undergo Michael addition with nucleophiles. This reaction served a convenient route to synthesize 4,5-disubstituted-l,2-benzoquinones (3a-c) and 6-substituted-3-hydroxy-4(1H)-pyridinones (6a-f) . |
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| Keywords: | Synthesis oxidation-Michael addition substituted 1 2-benzoquinone substituted 3-hydroxy-4 (1H)-pyridinone |
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