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

被引：0
|
作者：
Xie, Wen Lin [1 ]
Xiao, Chuang Ping [1 ]
Xie, Ling [1 ]
Zhou, Ying [1 ]
Li, Xue Feng [1 ]
Tang, Xu Fu [1 ]
Yuan, Chun Tao [1 ]
Qiu, Ming Hua [1 ]
机构：
[1] Hunan Univ Sci & Technol, Key Lab Theoret Chem & Mol Simulat, Sch Chem & Chem Engn, Hunan Prov Univ Key Lab QSAR QSPR,Minist Educ, Xiangtan 411201, Peoples R China
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2012年 / 38卷 / 07期
关键词：
Pyridinone; Mannich reaction; Oxidation; Michael addition; IRON;
D O I：
10.1007/s11164-012-0495-z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
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 H-1 NMR, ESI-MS, and IR, and elemental analysis.
引用
收藏
页码：1699 / 1705
页数：7
相关论文
共 50 条
  • [1] Synthesis of 4,5,6-trisubstituted 2,3-pyridinediones via Mannich reaction and oxidation–Michael addition of 3-hydroxy-2(1H)-pyridinones
    Wen Lin Xie
    Chuang Ping Xiao
    Ling Xie
    Ying Zhou
    Xue Feng Li
    Xu Fu Tang
    Chun Tao Yuan
    Ming Hua Qiu
    Research on Chemical Intermediates, 2012, 38 : 1699 - 1705
  • [2] Synthesis of 6-substituted-3-hydroxy-4-(1H)-pyridinones:: Oxidation-Michael addition of 3-hydroxy-4(1H)-pyridinones
    Li, MS
    Gu, LQ
    Huang, ZS
    Xiao, SH
    Ma, L
    TETRAHEDRON, 1999, 55 (08) : 2237 - 2244
  • [3] Directed aminomethylation of 3-hydroxy-2(1H)-pyridinones and 3-hydroxy-4(1H)-pyridinones: Synthesis of iso-deferiprone
    Patel, MK
    Fox, R
    Taylor, PD
    TETRAHEDRON, 1996, 52 (05) : 1835 - 1840
  • [4] Synthesis of substituted 1,2-benzoquinones and substituted 3-hydroxy-4 (1H) -pyridinones: Application of oxidation-Michael addition in organic synthesis
    李苗盛
    马林
    张小春
    黄志纾
    肖韶华
    古练权
    Chinese Journal of Chemistry, 1999, (04) : 377 - 383
  • [5] Synthesis of 4,5,6-trisubstituted 3-cyanopyridine-2(1H)-thiones based on alpha-substituted beta-diketones
    Frolova, NG
    Zavyalova, VK
    Litvinov, VP
    RUSSIAN CHEMICAL BULLETIN, 1996, 45 (11) : 2578 - 2580
  • [6] Synthesis of substituted 1,2-benzoquinones and substituted 3-hydroxy-4(1H)-pyridinones:: Application of oxidation -: Michael addition in organic synthesis
    Li, MS
    Ma, L
    Zhang, XC
    Huang, ZS
    Xiao, SH
    Gu, LQ
    CHINESE JOURNAL OF CHEMISTRY, 1999, 17 (04) : 377 - 383
  • [7] NOVEL 3-HYDROXY-2(1H)-PYRIDINONES - SYNTHESIS, IRON(III)-CHELATING PROPERTIES, AND BIOLOGICAL-ACTIVITY
    STREATER, M
    TAYLOR, PD
    HIDER, RC
    PORTER, J
    JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) : 1749 - 1755
  • [8] STUDIES ON PROTOTROPIC TAUTOMERISM IN NITROGEN HETEROCYCLIC COMPOUNDS .I. MANNICH REACTION OF 2(1H)-PYRIDONE AND 3-HYDROXY-2(1H)-PYRIDONE
    NAKAMURA, A
    KAMIYA, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1968, 16 (08) : 1466 - +
  • [9] Regioselective synthesis of 1,4,6-trisubstituted-2-pyridinones and 2,3-disubstituted (2H)-isoquinolin-1-ones via tandem Stille reaction/heterocyclisation
    Cherry, K
    Duchêne, A
    Thibonnet, J
    Parrain, JL
    Abarbri, M
    SYNTHESIS-STUTTGART, 2005, (14): : 2349 - 2356
  • [10] Oxa-Michael Addition Reactions of 3-hydroxy-2-azetidinones: Synthesis of 1, 3, 4-Trisubstituted-2-Azetidinones
    Sharma, Priyanka
    Mann, Maninderjeet Kaur
    Bhargava, Gaurav
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (06) : 471 - 476
12345