TiO2 Nanoparticles Catalyzed Chemoselective Synthesis of 2-Chloroquinolinyl-4-quinolinones and their Intramolecular Cyclization through Palladium Catalyzed Sonogashira Coupling Reaction

被引:3
|
作者
Kumar, Y. Suneel [1 ]
Khan, F. Nawaz [1 ]
机构
[1] VIT Univ, Vellore, Tamil Nadu, India
关键词
Chemoselective synthesis; Intramolecular cyclization; Sonogashira coupling reaction; SOLVENT-FREE CONDITIONS; CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES; EFFICIENT; 2'-AMINOCHALCONES; DERIVATIVES;
D O I
10.1007/s10562-017-1992-x
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The 2-chloro-3-formyl quinolines 1, were chemoselectivity and effectively converted into their corresponding 2-chloroquinolinyl-4-quinolinones 3 through Knoevenagel condensation/aza-Michael addition utilizing TiO2 nanoparticles. The Sonogashira coupling of 2-chloroquinolinyl moiety of the quinolinone, 3 gave unprecedented cyclised products 1,6-naphthyridines, 5 through cascade reaction in good yields and purity.
引用
收藏
页码:919 / 925
页数:7
相关论文
共 50 条
  • [21] Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones, -thione, and -selones, Catalyzed by TiO2 Nanoparticles
    Mohammadi, B.
    Behbahani, F. K.
    Marandi, G. B.
    Mirza, B.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (09) : 1319 - 1326
  • [22] Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines
    Liu, Bifu
    Gao, Hanling
    Yu, Yue
    Wu, Wanqing
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10319 - 10328
  • [23] Synthesis of Fluoro- and Perfluoroalkyl Arenes via Palladium-Catalyzed [4+2] Benzannulation Reaction
    Zatolochnaya, Olga V.
    Gevorgyan, Vladimir
    ORGANIC LETTERS, 2013, 15 (10) : 2562 - 2565
  • [24] CuSO4•5H2O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes
    Qi, Haitang
    Song, Guanglin
    Quan, Zhengjun
    Wang, Xicun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1855 - 1859
  • [25] Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles
    Arthuis, Martin
    Pontikis, Renee
    Florent, Jean-Claude
    ORGANIC LETTERS, 2009, 11 (20) : 4608 - 4611
  • [26] Synthesis of 2-Alkynyl 1,3,4-Oxadiazoles by Palladium-Catalyzed Cross-Coupling Reaction
    Salvanna, N.
    Das, Biswanath
    SYNLETT, 2014, 25 (14) : 2033 - 2035
  • [27] ZnCl2-Catalyzed Intramolecular Cyclization Reaction of 2-Aminochalcones Using Polymer-Supported Selenium Reagent: Synthesis of 2-Phenyl-4-quinolones and 2-Phenyl-2,3-dihydroquinolin-4(1H)-one
    Tang, E.
    Chen, Bangzheng
    Zhang, Lianpeng
    Li, Wen
    Lin, Jun
    SYNLETT, 2011, (05) : 707 - 711
  • [28] A Highly Stereoselective Synthesis of E-(But-1-en-3-yne-1-sulfonyl) hetarenes and Disubstituted 2-Benzothiazolyl Alkynes by Palladium Catalyzed Sonogashira Type Coupling of 2-Chlorovinylsulfones
    Visnevska, Julija
    Belyakov, Sergey
    Abele, Edgars
    LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (04) : 250 - 256
  • [29] Highly Efficient Construction of 2-Fluoroalkyl Quinolines through a Palladium-Catalyzed 6-endo-trig Heck Cyclization Reaction
    Han, Fangwai
    Yang, Wenqing
    Zhao, Aichun
    Zheng, Ruihong
    Ji, Chenhui
    Liu, Xinqi
    Liu, Guiyan
    Chen, Chen
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) : 1124 - 1131
  • [30] Stereoselective Synthesis of β-Amino Ketones via Direct Mannich-Type Reaction Catalyzed with SO42-/TiO2 and SO42-/Nano TiO2
    Samet, Masoud
    Eftekhari-Sis, Bagher
    Hashemi, Mohammed M.
    Farmad, Fateme
    SYNTHETIC COMMUNICATIONS, 2009, 39 (24) : 4441 - 4453