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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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Abstract

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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Acknowledgments

We are grateful for financial support from the Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education (no. LKF0905) and the science and technology project of Hunan Province (no. 2011SK3122).

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  1. 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, Hunan University of Science and Technology, Xiangtan, 411201, China

    Wen Lin Xie, Chuang Ping Xiao, Ling Xie, Ying Zhou, Xue Feng Li, Xu Fu Tang, Chun Tao Yuan & Ming Hua Qiu

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  1. Wen Lin Xie
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  2. Chuang Ping Xiao
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  3. Ling Xie
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  4. Ying Zhou
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  6. Xu Fu Tang
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  7. Chun Tao Yuan
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  8. Ming Hua Qiu
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Correspondence to Wen Lin Xie.

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Xie, W.L., Xiao, C.P., Xie, L. et al. Synthesis of 4,5,6-trisubstituted 2,3-pyridinediones via Mannich reaction and oxidation–Michael addition of 3-hydroxy-2(1H)-pyridinones. Res Chem Intermed 38, 1699–1705 (2012). https://doi.org/10.1007/s11164-012-0495-z

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  • DOI: https://doi.org/10.1007/s11164-012-0495-z

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