Substituent-controlled chemoselective synthesis of multi-substituted pyridones via a one-pot three-component cascade reaction

被引：26
|
作者：
Liu, Shitao [1 ]
Li, Jisen [1 ]
Lin, Junjie [1 ]
Liu, Fujun [1 ]
Liu, Teng [2 ]
Huang, Chao [1 ]
机构：
[1] Yunnan Minzu Univ, Key Lab Intelligent Supramol Chem Univ Yunnan Pro, Sch Chem & Environm, Natl & Local Joint Engn Res Ctr Green Preparat Te, Kunming 650500, Yunnan, Peoples R China
[2] Qujing Normal Univ, Ctr Yunnan Guizhou Plateau Chem Funct Mat & Pollu, Qujing 655011, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 06期
基金：
中国国家自然科学基金;
关键词：
QUINONE IMINE KETALS; SOLVENT-FREE; 2-PYRIDONE SYNTHESIS; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; FACILE SYNTHESIS; DOMINO; CONSTRUCTION; DERIVATIVES; ENAMINONES;
D O I：
10.1039/c9ob02456e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and concise one-pot strategy for the synthesis of multisubstituted pyridones via a one-pot three-component cascade reaction catalyzed by Cs2CO3 under solvent-free conditions has been developed. The substituent-controlled chemoselective cycloaddition process involved steps including a Michael addition/ethanol elimination/intermolecular cyclization sequence utilizing anilines, diethyl acetylenedicarboxylate, and diethyl ethoxymethylenemalonate. In doing so, various 2-pyridone and 4-pyridone species (41 examples) could be obtained in good to excellent yields.
引用
收藏
页码：1130 / 1134
页数：5
相关论文
共 50 条
  • [41] One-pot cascade polycondensation and Passerini three-component reactions for the synthesis of functional polyesters
    Alkan, Burcu
    Daglar, Ozgun
    Luleburgaz, Serter
    Gungor, Begum
    Gunay, Ufuk Saim
    Hizal, Gurkan
    Tunca, Umit
    Durmaz, Hakan
    POLYMER CHEMISTRY, 2022, 13 (02) : 258 - 266
  • [42] One-Pot Three-Component Barbier-Type Reaction for the Synthesis of β-Nitroamines
    Soengas, Raquel G.
    Silva, Artur M. S.
    SYNLETT, 2013, 24 (15) : 1949 - 1952
  • [43] Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One-pot Three-component Sequential Cascade Reactions
    Zhao, Bo-Liang
    Du, Da-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (14) : 3412 - 3419
  • [44] Synthesis of Dithiocarbamate-Functionalized Aliphatic Sulfonyl Fluoride via a One-Pot Three-Component Reaction
    Mohamedy, Heba H.
    Fayad, Eman
    Katouah, Hanadi A.
    Qin, Hua-Li
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (11)
  • [45] Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water
    Jin, Shuai-Shuai
    Ding, Mao-Hua
    Guo, Hong-Yun
    HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 139 - 143
  • [46] Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction
    Malathi, Visarapu
    Reddy, Pedavenkatagari Narayana
    Padmaja, Pannala
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (09) : 721 - 726
  • [47] Synthesis of benzofuro[2,3-c]pyridines via a one-pot three-component reaction
    Hu, Jiaxing
    Deng, Zhihong
    Zhang, Xueqiong
    Zhang, Fanglin
    Zheng, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (27) : 4885 - 4889
  • [48] One-pot three-component synthesis of quinazolines via a copper-catalysed oxidative amination reaction
    Duan, Tiantian
    Zhai, Tianran
    Liu, Huanhuan
    Yan, Zilong
    Zhao, Yue
    Feng, Lei
    Ma, Chen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (27) : 6561 - 6567
  • [49] One-Pot Synthesis of Fused [1,6]Naphthyridine Derivatives via Three-Component Reaction
    Kumar, Adhiyaman Kottai Munusamy Magesh Selva
    Dhivya, Paul
    Rajendran, Subramanian Parameswaran
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2017, 64 (02) : 138 - 142
  • [50] Synthesis of multisubstituted arylsulfones via a one-pot, three-component [3+3] benzannulation reaction
    Tang, Xiang-Zheng
    Liang, Jie
    Zhang, Xue-Jing
    Sun, Raymond Wai-Yin
    Yan, Ming
    Chan, Albert S. C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4753 - 4760
12345