Practical Synthesis of Functionalized Chromeno[3,4-c]pyridine Derivatives via a CuCl2-Catalyzed Tandem Reaction of the Blaise Reaction Intermediates and 3-Cyanocoumarins

被引：4
|
作者：
Fan, Yangyang [1 ]
Zheng, Lei [1 ]
Yang, Zhaohai [1 ]
Li, Jian-Jun [1 ,2 ]
Chen, Zhiwei [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2018年 / 29卷 / 07期
基金：
中国国家自然科学基金;
关键词：
tandem reaction; CuCl2-catalyzed; Blaise reaction intermediates; 3-cyanocoumarins; chromeno[3,4-c]pyridines; ONE-POT SYNTHESIS; POLYSUBSTITUTED PYRIDINES; MULTICOMPONENT SYNTHESIS; BIOLOGICAL-ACTIVITY; ANTITUMOR AGENTS; COUMARINS; CYCLIZATION;
D O I：
10.1055/s-0036-1591535
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This work discloses a novel and efficient protocol for the construction of functionalized chromeno[3,4-c]pyridine derivatives from the Blaise reaction intermediates and 3-cyanocoumarins through a CuCl2-catalyzed sequential Michael addition/intramolecular cyclization/oxidative aromatization reaction. This new method shows the advantages of mild reaction conditions, easy workup, nonchromato-graphic purification technique, good functional group tolerance, and moderate to good yields.
引用
收藏
页码：959 / 963
页数：5
相关论文
共 50 条
  • [41] Three-Component Tandem Reaction Involving Acid Chlorides, Terminal Alkynes, and 2-Aminoindole Hydrochlorides: Synthesis of α-Carboline Derivatives in Aqueous Conditions via Regioselective [3+3] Cyclocondensation
    Gupta, Sahaj
    Kumar, Brijesh
    Kundu, Bijoy
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) : 10154 - 10162
  • [42] Versatile synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives via intra-molecular Friedel-Crafts reaction with trifluoromethanesulfonic acid
    Murashige, Ryo
    Ohtsuka, Yoko
    Sagisawa, Kazuki
    Shiraishi, Mitsuru
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3410 - 3412
  • [43] Chiral bifunctional squaramide catalyzed asymmetric tandem Michael-cyclization reaction: efficient synthesis of optically active 2-amino-4H-chromene-3-carbonitrile derivatives
    Hu, Keling
    Lu, Aidang
    Wang, Youming
    Zhou, Zhenghong
    Tang, Chuchi
    TETRAHEDRON-ASYMMETRY, 2013, 24 (15-16) : 953 - 957
  • [44] Asymmetric Synthesis of Spiro[Azetidine-3,3′-Indoline]-2,2′-Diones via Copper(I)-Catalyzed Kinugasa/C-C Coupling Cascade Reaction
    Zhong, Xianqiang
    Huang, Meirong
    Xiong, Huilan
    Liang, Yuzhen
    Zhou, Wei
    Cai, Qian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (42)
  • [45] Inorganic base catalyzed synthesis of (2-amino-3-cyano-4H-chromene-4-yl) phosphonate derivatives via multi-component reaction under mild and efficient conditions
    Dai, Peng
    Zha, Gaofeng
    Lai, Xiaoyan
    Liu, Wei
    Gan, Qianwen
    Shen, Yongcun
    RSC ADVANCES, 2014, 4 (108): : 63420 - 63424
  • [46] Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction
    Altieri, Elisa
    Cordaro, Massimiliano
    Grassi, Giovanni
    Risitano, Francesco
    Scala, Angela
    TETRAHEDRON, 2010, 66 (49) : 9493 - 9496
  • [47] Synthesis and neurotropic activity of 6-thio-substituted pyrano[3,4-c]pyridine and 1-aminopyrano[4,3-d]-thieno[2,3-b]pyridine derivatives and 9-substituted pyrido[2,3-b]thieno[3,2-d]pyrimidines
    E. G. Paronikyan
    Sh. F. Akopyan
    A. S. Noravyan
    I. A. Dzhagatspanyan
    I. M. Nazaryan
    A. G. Akopyan
    Pharmaceutical Chemistry Journal, 2010, 44 : 183 - 185
  • [48] SYNTHESIS AND NEUROTROPIC ACTIVITY OF 6-THIO-SUBSTITUTED PYRANO[3,4-c]PYRIDINE AND 1-AMINOPYRANO[4,3-d]-THIENO[2,3-b]PYRIDINE DERIVATIVES AND 9-SUBSTITUTED PYRIDO[2,3-b]THIENO[3,2-d]PYRIMIDINES
    Paronikyan, E. G.
    Akopyan, Sh. F.
    Noravyan, A. S.
    Dzhagatspanyan, I. A.
    Nazaryan, I. M.
    Akopyan, A. G.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2010, 44 (04) : 183 - 185
  • [49] Using of ZnCl2/AlCl3-SiO2 Catalyzed for One-Pot and Tree Substituted Synthesis of 1,4-Dihydropyridine Derivatives Via Hantzsch Reaction
    Asghariganjeh, Mohammad R.
    Nasirveise, Parastoo
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (05) : 2937 - 2938
  • [50] Ultrasound-assisted synthesis of highly functionalized benzo[1,3]thiazine via Cu-catalyzed intramolecular C-H activation reaction from isocyanides, aniline-benzoyl(acetyl) isothiocyanate adduct
    Nematpour, Manijeh
    Rezaee, Elham
    Jahani, Mehdi
    Tabatabai, Sayyed Abbas
    ULTRASONICS SONOCHEMISTRY, 2019, 50 : 1 - 5
12345