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

WL Xie, CP Xiao, L Xie, Y Zhou, XF Li, XF Tang…

Index: Xie, Wen Lin; Xiao, Chuang Ping; Xie, Ling; Zhou, Ying; Li, Xue Feng; Tang, Xu Fu; Yuan, Chun Tao; Qiu, Ming Hua Research on Chemical Intermediates, 2012 , vol. 38, # 7 p. 1699 - 1705

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Abstract

Abstract 4-Substituted 3-hydroxy-2 (1 H)-pyridinones 2 were prepared by Mannich reaction of 3-hydroxy-2 (1 H)-pyridinones with secondary amines and formaldehyde. The isolated products were then reacted with aromatic amines in the presence of NaIO 3 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 1 H NMR, ESI-MS, ...