Efficient Synthesis of Pyridin-2(1H)-ones From a Series of Readily Available Enaminones Under Mild Conditions

被引：3

作者：

Gao, Bao-chang ^{[1
,2
]}

Sun, Yu-feng ^{[2
]}

Wang, Jun ^{[1
]}

Zu, Li-wu ^{[1
]}

Zhang, Xu ^{[2
]}

Liu, Wen-bin ^{[1
]}

机构：

[1] Harbin Engn Univ, Coll Mat Sci & Chem Engn, Key Lab Superlight Mat & Surface Technol, Inst Composite Mat,Minist Educ, Harbin 150001, Heilongjiang, Peoples R China

[2] Heilongjiang Acad Sci, Daqing Branch, Daqing 163319, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2018年 / 55卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; CYCLOADDITION; PYRIDONE; FACILE; ROUTE;

D O I：

10.1002/jhet.3333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of substituted pyridin-2(1H)-ones has been developed by the reaction of readily available enaminones with malononitrile in ethanol at room temperature in yields of 85-95%. This protocol, which combines construction and modification of the pyridin-2(1H)-ones ring under Vilsmeier conditions (dimethylformamide/POCl3), increases the structural diversity of the final products from readily available materials.

引用

页码：2732 / 2736

页数：5

共 50 条

[1] Vilsmeier Reaction of Enaminones: Efficient Synthesis of Halogenated Pyridin-2(1H)-ones
Zhang, Rui
Zhang, Dingyuan
Guo, Yongli
Zhou, Guangyuan
Jiang, Zijiang
Dong, Dewen
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23): : 9504 - 9507
[2] A Practical Synthesis of 1-Azine-pyridin-2(1H)-ones from Azine N-oxides and Pyridin-2(1H)-ones under Mild Reaction Conditions
Bi, Wen-Zhu
Zhang, Wen-Jie
Li, Zi-Jie
Feng, Su-Xiang
Chen, Xiao-Lan
Qu, Ling-Bo
[J]. CHEMISTRYSELECT, 2020, 5 (45): : 14320 - 14323
[3] A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from β-oxo amides under Vilsmeier conditions
Xiang, Dexuan
Wang, Kewei
Liang, Yongjiu
Zhou, Guangyuan
Dong, Dewen
[J]. ORGANIC LETTERS, 2008, 10 (02) : 345 - 348
[4] Synthesis and characterization of new N-alkylated pyridin-2(1H)-ones
Sharma, Atul Kumar
Yadav, Preeti
Chand, Karam
Sharma, Sunil K.
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2016, 55 (04): : 492 - 500
[5] SYNTHESIS OF PYRIDIN-2(1H)-ONES BY THE INTRAMOLECULAR CYCLIZATION OF AMIDES OF β-ENAMINO KETONES
Goncharov, D. S.
Kostuchenko, A. S.
Fisyuk, A. S.
[J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 793 - 795
[6] Synthesis of pyridin-2(1H)-ones by the intramolecular cyclization of amides of β-enamino ketones
D. S. Goncharov
A. S. Kostuchenko
A. S. Fisyuk
[J]. Chemistry of Heterocyclic Compounds, 2009, 45 : 793 - 795
[7] Efficient One-Pot Synthesis of 1,3-Disubstituted Pyridin-2(1H)-ones from α-Hydroxyketene S,S-Acetals under Vilsmeier Conditions
Liu, Jun
Liang, Deqiang
Wang, Mang
Liu, Qun
[J]. SYNTHESIS-STUTTGART, 2008, (22): : 3633 - 3638
[8] Synthesis of 1-(1-Arylvinyl)pyridin-2(1H)-ones from Ketones and 2-Fluoropyridine
Kawamoto, Takuji
Ikeda, Shunya
Kamimura, Akio
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19): : 13783 - 13789
[9] Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*
A. S. Fisyuk
Y. P. Bogza
N. V. Poendaev
D. S. Goncharov
[J]. Chemistry of Heterocyclic Compounds, 2010, 46 : 844 - 849
[10] A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones from α-oxoketene-S,S-acetals
Yang, Xiuyun
Cheng, Yanyan
Zhao, Fei
Li, Yunhui
Ding, Yuanli
Liang, Yongjiu
Gan, Fengjiao
Dong, Dewen
[J]. TETRAHEDRON, 2011, 67 (43) : 8343 - 8347

← 1 2 3 4 5 →