Synthesis of 4,5,6-trisubstituted 2,3-pyridinediones via Mannich reaction and oxidation–Michael addition of 3-hydroxy-2(1H)-pyridinones

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作者
Wen Lin Xie
Chuang Ping Xiao
Ling Xie
Ying Zhou
Xue Feng Li
Xu Fu Tang
Chun Tao Yuan
Ming Hua Qiu
机构
[1] Hunan University of Science and Technology,Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Provincial University Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering
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Pyridinone; Mannich reaction; Oxidation; Michael addition;
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摘要
4-Substituted 3-hydroxy-2(1H)-pyridinones 2 were prepared by Mannich reaction of 3-hydroxy-2(1H)-pyridinones with secondary amines and formaldehyde. The isolated products were then reacted with aromatic amines in the presence of NaIO3 as oxidant via oxidation–Michael addition to yield 4,5,6-trisubstituted-2,3-pyridinediones 3 in good yields (80.2–88.9%). The structures of the products were characterized by 1H NMR, ESI-MS, and IR, and elemental analysis.
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页码:1699 / 1705
页数:6
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