Pd/C-Mediated Dual C-C Bond Forming Reaction in Water: Synthesis of 2,4-Dialkynylquinoline

被引:3
|
作者
Reddy, Ellanki A. [2 ,3 ]
Islam, Aminul [3 ]
Mukkanti, K. [2 ]
Venu, Bolla K. [3 ]
Pal, Manojit [1 ]
机构
[1] Matrix Labs Ltd, R&D Ctr, New Drug Discovery, Jinnaram Mandal 502325, Andra Pradesh, India
[2] JNT Univ, Inst Sci & Technol, Div Chem, Hyderabad 500072, Andhra Pradesh, India
[3] Dr Reddys Labs Ltd, Hyderabad 500049, Andhra Pradesh, India
关键词
quinoline; palladium; charcoal; copper; C-C bond; alkyne; COUPLING REACTIONS;
D O I
10.1590/S0103-50532010000900012
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd/C facilitated dual C-C bond forming reaction between 2,4-diiodoquinoline and terminal alkynes in water providing a practical and one-step synthesis of 2,4-dialkynylquinolines. A number of related quinoline derivatives were prepared in good to excellent yields using this water-based methodology. The use of other palladium catalysts and solvents was examined and the mechanism of the reaction has been discussed.
引用
收藏
页码:1681 / 1687
页数:7
相关论文
共 50 条
  • [31] ASYMMETRIC CATALYSIS OF C-C BOND FORMING REACTIONS
    RAJANBABU, TV
    CASALNUOVO, AL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 70 - CARB
  • [32] SYNTHESIS AND UNUSUAL REACTION OF C-C BOND-CLEAVAGE FOR BISISOCHROMENES
    DOROFEENKO, GN
    SAFARYAN, GP
    VOLOSHINOVA, VF
    OKHLOBYSTIN, OY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1976, (07): : 999 - 1000
  • [33] Cascade C-H Activation and Two C-C Bond Forming in Reaction of Azalutetacyclopentadiene with 2-Methylbenzonitriles
    Chai, Zhengqi
    Lv, Ze-Jie
    Liu, Wei
    Yang, Jinxiao
    Wei, Junnian
    Zhang, Wen-Xiong
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (53)
  • [34] Pd/C-mediated depropargylation of propargyl ethers/amines in water
    Rambabu, D.
    Bhavani, S.
    Swamy, Nalivela Kumara
    Rao, M. V. Basaveswara
    Pal, Manojit
    TETRAHEDRON LETTERS, 2013, 54 (09) : 1169 - 1173
  • [35] Diastereoselective construction of azetidin-2-ones by electrochemical intramolecular C-C bond forming reaction
    Minato, Daishirou
    Mizuta, Satoshi
    Kuriyama, Masami
    Matsumura, Yoshihiro
    Onomura, Osamu
    TETRAHEDRON, 2009, 65 (47) : 9742 - 9748
  • [36] A new C-C bond forming annulation reaction leading to pH switchable heterocycles
    Kitson, Philip J.
    Parenty, Alexis D. C.
    Richmond, Craig J.
    Long, De-Liang
    Cronin, Leroy
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4067 - 4069
  • [37] A catalytic C-C bond-forming reaction between aliphatic fluorohydrocarbons and arylsilanes
    Luehmann, Nicole
    Panisch, Robin
    Mueller, Thomas
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (07) : 533 - 537
  • [38] Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines
    Pilgrim, Ben S.
    Gatland, Alice E.
    Esteves, Carlos H. A.
    McTernan, Charlie T.
    Jones, Geraint R.
    Tatton, Matthew R.
    Procopiou, Panayiotis A.
    Donohoe, Timothy J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (03) : 1065 - 1090
  • [39] ORGN 374-Synthesis of acyl benzothiophenes via clean chemistry C-C bond forming reaction
    Pal, Sarbani
    Khan, Mohamma Ashrafuddin
    Bindu, P.
    Dubey, P. K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [40] ORGN 553-Pd-catalyzed C-C bond forming reactions of a thymidine arylsulfonate
    Kang, Soon Bang
    De Clercq, Erik
    Lakshman, Mahesh K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234