One-pot synthesis of quinoline-based tetracycles by a tandem three-component reaction

被引:57
|
作者
Che, Chao
Xiang, Jing
Wang, Guo-Xin
Fathi, Reza
Quan, Jun-Min
Yang, Zhen [1 ]
机构
[1] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Shenzhen Grad Sch,Lab Chem Genom, Beijing 100871, Peoples R China
[2] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Coll Chem,BNLMS, Beijing 100871, Peoples R China
[3] XTL Biopharmaceut Inc, New York, NY 10989 USA
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2007年 / 9卷 / 06期
关键词
D O I
10.1021/cc070058a
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A practical one-pot synthetic strategy for the efficient synthesis of a range of structurally interesting and bioactive quinoline-based tetracycles has been developed. A key step in the synthesis is a tandem three-component reaction of heteroaromatic amine, methyl 2-formylbenzoate and (t)butyl isonitrile, followed by TFA-mediated lactamization via intramolecular aminolysis of an adjacent ester. Results related to a kinase-panel screening for several selected compounds are also discussed in this article.
引用
收藏
页码:982 / 989
页数:8
相关论文
共 50 条
  • [41] A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
    Ozcan, Sevil
    Dengiz, Cagatay
    Deliomeroglu, Murat K.
    Sahin, Ertan
    Balci, Metin
    [J]. TETRAHEDRON LETTERS, 2011, 52 (13) : 1495 - 1497
  • [42] One-Pot, Three-Component Coupling Approach to the Synthesis of α-Iminocarboxamides
    Masui, Hisashi
    Fuse, Shinichiro
    Takahashi, Takashi
    [J]. ORGANIC LETTERS, 2012, 14 (16) : 4090 - 4093
  • [43] Three-Component, One-Pot Synthesis of New Functionalized Pyrrolines
    Asghari, Sakineh
    Qandalee, Mohammad
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (14) : 2172 - 2177
  • [44] An efficient and convenient approach to the synthesis of benzopyrans by a three-component coupling of one-pot reaction
    Jin, TS
    Xiao, JC
    Wang, SJ
    Li, TS
    Song, XR
    [J]. SYNLETT, 2003, (13) : 2001 - 2004
  • [45] A Simple Synthesis of Functionalized 3-Bromocoumarins by a One-Pot Three-Component Reaction
    Audisio, Davide
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) : 1046 - 1051
  • [46] One-Pot, Three-Component Synthesis of a Library of New Pyrrolo[1,2-a]quinoline Derivatives
    Georgescu, Emilian
    Caira, Mino R.
    Georgescu, Florentina
    Draghici, Bogdan
    Popa, Marcel M.
    Dumitrascu, Florea
    [J]. SYNLETT, 2009, (11) : 1795 - 1799
  • [47] ONE-POT SYNTHESIS OF ISOINDOLINONES VIA THREE-COMPONENT MANNICH/LACTAMIZATION CASCADE REACTION
    Zhang, Haoyi
    Leng, Yixin
    Liu, Wenjing
    Duan, Wenhu
    [J]. SYNTHETIC COMMUNICATIONS, 2012, 42 (08) : 1115 - 1127
  • [48] The synthesis of 2-substituted azoles through a one-pot three-component reaction
    Deng, YJ
    Hlasta, DJ
    [J]. TETRAHEDRON LETTERS, 2002, 43 (02) : 189 - 192
  • [49] EFFICIENT SYNTHESIS OF PURINE DERIVATIVES BY ONE-POT THREE-COMPONENT MANNICH TYPE REACTION
    Zhang, Qian
    Ma, Bai-Wei
    Huang, Yong-Zhen
    Wang, Qian-Qian
    Wang, Xing-Xing
    Qu, Gui-Rong
    Guo, Hai-Ming
    [J]. HETEROCYCLES, 2013, 87 (10) : 2081 - 2091
  • [50] Efficient One-Pot Three-Component Synthesis of Monomethine Cyanine Dyes with Quinoline Nucleus and Their Spectral Properties
    Fu, Y. L.
    Zhang, B. R.
    Wang, S.
    Gao, X. X.
    Wang, L. Y.
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (02) : 489 - 494