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
[21]   Formal Acylamination of Nitroalkenes in Aqueous Medium for the Synthesis of 2-Aryl-3-nitro-2,3-dihydroquinolin-4(1H)-ones [J].
Chaturvedi, Atul Kumar ;
Rastogi, Namrata .
SYNTHESIS-STUTTGART, 2015, 47 (02) :249-255
[22]   A facile and efficient synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process [J].
Liu, Xiong-Li ;
Zhang, Wen-Hui ;
Yao, Zhen ;
Liu, Xiong-Wei ;
Peng, Li-Jun ;
Zhao, Zhi ;
Lu, Yi ;
Zhou, Ying ;
Yuan, Wei-Cheng .
TETRAHEDRON, 2015, 71 (50) :9483-9495
[23]   5',6',7',8'-Tetrahydro-1'H,3'H-spiro[cyclohexane-1,2'-quinazolin]-4'-one in Mannich reaction [J].
Markov, V. I. ;
Farat, O. K. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (06) :925-930
[24]   5',6',7',8'-Tetrahydro-1'H,3'H-spiro[cyclohexane-1,2'-quinazolin]-4'-one in Mannich reaction [J].
V. I. Markov ;
O. K. Farat .
Chemistry of Heterocyclic Compounds, 2012, 48 :925-930
[25]   Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones [J].
Kang, Seongil ;
Park, Subin ;
Kim, Kyung-su ;
Song, Changsik ;
Lee, Yunmi .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) :2694-2705
[26]   Catalyst free Michael addition of 3-methyl-2-pyrazolin-5-one to β-nitrostyrenes 'on water': a green protocol for facile synthesis of 4-(1-aryl-2-nitroethyl)-3-methyl-1H-pyrazol-5-ol [J].
Meshram, H. M. ;
Kumar, Nandigama Satish ;
Nanubolu, Jagadeesh Babu ;
Rao, L. Chandrasekhara ;
Rao, N. Nageswara .
TETRAHEDRON LETTERS, 2013, 54 (45) :5941-5944
[27]   New Strategy for the Synthesis of 5-Aryl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones and Their Sulfur Analogues [J].
Jalilzadeh, Mohammad ;
Pesyan, Nader Noroozi .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (09) :3382-3388
[28]   Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I2/K2CO3 in water: a new and green approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones [J].
Azimi, Seyedeh Bahareh ;
Azizian, Javad .
TETRAHEDRON LETTERS, 2016, 57 (02) :181-184
[29]   Sulfonated carbon/silica composite functionalized Lewis acids for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles, 3,4-dihydropyrimidin-2(1H)-ones and for Michael addition of indole to α,β-unsaturated ketones [J].
Gupta, Princy ;
Paul, Satya .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 352 :75-80
[30]   Versatile Quinazolinone Synthesis: N-Bromosaccharin-Catalyzed Divergence in 2,3-Dihydroquinazolin-4(1H)-one and Quinazolin-4(3H)-one Formation [J].
Hutait, Samiran ;
Maikhuri, Vipin K. ;
Kumar Pandey, Avadhesh ;
Shukla, Poonam ;
Srivastava, Suman .
CHEMISTRYSELECT, 2024, 9 (12)