Transition-metal-free highly efficient synthesis of 2-pyridones from β-keto amides and ynals

被引:6
作者
Chen, Zhengwang [1 ]
Liu, Jiayang [1 ]
Jin, Caiju [1 ]
Tan, Qi [1 ]
Ye, Min [1 ]
机构
[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Jiangxi, Peoples R China
关键词
Pyridone; Ynal; Annulation reaction; Enyneamide; CATALYZED N-ARYLATION; 2+2+2 CYCLOADDITION; ISOCYANATES; ALKYNES; ACCESS;
D O I
10.1016/j.tetlet.2019.04.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient annulation reaction was developed, affording 2-pyridones in good to excellent yields. A variety of substituted beta-keto amides and ynals were well tolerated, and especially the transformation produced water as only by-product under transition-metal-free conditions. Furthermore, the conjugated enyneamides were achieved from beta-cyano amides and ynals in high yields. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1265 / 1267
页数:3
相关论文
共 33 条
[1]   Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ORGANIC LETTERS, 2011, 13 (12) :3278-3281
[2]   Cooperative Heterogeneous Organocatalysis and Homogeneous Metal Catalysis for the One-Pot Regioselective Synthesis of 2-Pyridones [J].
Allais, Christophe ;
Basle, Olivier ;
Grassot, Jean-Marie ;
Fontaine, Maxime ;
Anguille, Stephane ;
Rodriguez, Jean ;
Constantieux, Thierry .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) :2084-2088
[3]   Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (04) :643-646
[4]   Construction of Fully Substituted 2-Pyridone Derivatives via Four-Component Branched Domino Reaction Utilizing Microwave Irradiation [J].
Bai, Hairui ;
Sun, Rongrong ;
Liu, Shitao ;
Yang, Lijuan ;
Chen, Xuebing ;
Huang, Chao .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) :12535-12548
[5]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[6]   Cobalt-mediated macrocyclizations.: Facile synthesis of 2-oxo pyridinophanes via [2+2+2] cycloaddition of α,ω-diynes and isocyanates [J].
Boñaga, LVR ;
Zhang, HC ;
Gauthier, DA ;
Reddy, I ;
Maryanoff, BE .
ORGANIC LETTERS, 2003, 5 (24) :4537-4540
[7]   Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines [J].
Chen, Zhengwang ;
Liang, Pei ;
Ma, Xiaoyue ;
Luo, Haiqing ;
Xu, Guohai ;
Liu, Tanggao ;
Wen, Xiaowei ;
Zheng, Jing ;
Ye, Hui .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (03) :1630-1639
[8]   Synthesis of Pyridin-2(1H)-one Derivatives via Enamine Cyclization [J].
Chikhalikar, Sandip ;
Bhawe, Vijay ;
Ghotekar, Bhausaheb ;
Jachak, Madhukar ;
Ghagare, Maruti .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :3829-3836
[9]   Synthesis of functionalized 2-pyridones via Michael addition and cyclization reaction of amines, alkynes and dialkyl acetylene dicarboxylates [J].
Chong, Qinglei ;
Xin, Xiaoyi ;
Wang, Chunxiang ;
Wu, Fan ;
Wan, Boshun .
RSC ADVANCES, 2013, 3 (44) :21222-21226
[10]   Access to sulfonylated furans or imidazo[1,2-a]pyridines via a metal-free three-component, domino reaction [J].
Cui, Zhiming ;
Zhu, Baofu ;
Li, Xuechen ;
Cao, Hua .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14) :2219-2223