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
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
来源
Research on Chemical Intermediates | 2012年 / 38卷
关键词
Pyridinone; Mannich reaction; Oxidation; Michael addition;
D O I
暂无
中图分类号
学科分类号
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.
引用
收藏
页码:1699 / 1705
页数:6
相关论文
共 50 条
[31]   Facile and efficient synthesis of 4′-thioxo-1′,3,3′,4,4′,6′-hexahydro-1H,2′H-spiro(naphthalene-2,5′-pyrimidin)1-ones in a three-component Mannich-type reaction [J].
Jagodzinski, Tadeusz S. ;
Westerlich, Slawomir .
ARKIVOC, 2013, :294-303
[32]   Synthesis, characterization, and application of Fe3O4-SA-PPCA as a novel nanomagnetic reusable catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines [J].
Ghorbani-Choghamarani, Arash ;
Azadi, Gouhar .
RSC ADVANCES, 2015, 5 (13) :9752-9758
[33]   Polyfluorinated hydrazones in organic synthesis .2. Oxidation of 1,1,1,5,5,5-hexafluoro-4-trifluoromethylpentane-2,3-dione bishydrazone. Synthesis and structure of 1-amino-5-trifluoromethyl-4-(1,1,1,3,3,3-hexafluoroisopropyl)-1,2,3-triazole [J].
Bargamov, GG ;
Lysenko, KA ;
Bargamova, MD ;
Struchkov, YT .
RUSSIAN CHEMICAL BULLETIN, 1995, 44 (12) :2361-2363
[34]   Synthesis of 3,4-dihydropyrimidin-2(1H)-one via one-pot Biginelli reaction under solvent-free conditions [J].
Peng, Huan ;
Hu, Yulin ;
Xing, Rong ;
Fang, Dong .
MONATSHEFTE FUR CHEMIE, 2015, 146 (12) :2053-2058
[35]   Synthesis of substituted nortrop-2-enes and 3-vinylpyridin-2-ones via reaction of 1,2,3,4,5,6,7-heptamethoxycarbonylcycloheptatriene with primary amines [J].
Tomilov, Yury V. ;
Platonov, Dmitry N. ;
Okonnishnikova, Galina P. .
TETRAHEDRON LETTERS, 2009, 50 (40) :5605-5608
[36]   One-Pot Organocatalytic Asymmetric Synthesis of 1H-Pyrrolo[1,2a]indol-3(2H)-ones via a Michael-Hemiaminalization-Oxidation Sequence [J].
Enders, Dieter ;
Wang, Chuan ;
Yang, Xuena ;
Raabe, Gerhard .
SYNLETT, 2011, (04) :469-472
[37]   Synthesis of 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3,5′-pyrroline]-2,3′-dione via one-pot reaction of arylamines, acetone, and isatins [J].
Sun, Yan ;
Sun, Jing ;
Yan, Chao-Guo .
TETRAHEDRON LETTERS, 2012, 53 (28) :3647-3649
[38]   Synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component reaction catalyzed by l-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate (supported on silica gel) as novel and recoverable catalyst [J].
Ghorbani-Choghamarani, Arash ;
Zamani, Parisa .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (04) :607-613
[39]   Synthesis, characterization, DNA interaction and cleavage, and in vitro cytotoxicity of copper(II) mixed-ligand complexes with 2-phenyl-3-hydroxy-4(1H)-quinolinone [J].
Buchtik, Roman ;
Travnicek, Zdenek ;
Vanco, Jan ;
Herchel, Radovan ;
Dvorak, Zdenek .
DALTON TRANSACTIONS, 2011, 40 (37) :9404-9412
[40]   Mannich reaction in the synthesis of N,S-containing heterocycles. 15. Multicomponent cascade synthesis of 3,4,6a,7,8,9,10,10a-octahydro-2H,6H-pyrimido[4′,5′:4,5]pyrido[2,1-b][1,3,5]thia(selena)-diazine derivatives [J].
Frolov, K. A. ;
Dotsenko, V. V. ;
Krivokolysko, S. G. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 48 (10) :1555-1561