Iron-Catalyzed Tandem Reactions of Aldehydes, Terminal Alkynes, and Primary Amines as a Strategy for the Synthesis of Quinoline Derivatives

被引:48
|
作者
Zhang, Yicheng [1 ]
Li, Pinhua [1 ]
Wang, Lei [1 ,2 ]
机构
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
C-C BOND; SULFIDE OXIDATION; HYDROGEN-PEROXIDE; CROSS-COUPLINGS; EFFICIENT; QUINAZOLINE; HYDROSILYLATION; ARYLATION;
D O I
10.1002/jhet.417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
FeCl3-catalyzed three-component tandem condensation/addition/cyclization/oxidation reactions of aldehydes, terminal alkynes, and primary amines have been developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple starting materials. A possible reaction mechanism was proposed.
引用
收藏
页码:153 / 157
页数:5
相关论文
共 50 条
  • [21] Mercurous chloride catalyzed Mannich condensation of terminal alkynes with secondary amines and aldehydes
    Li, PH
    Wang, L
    CHINESE JOURNAL OF CHEMISTRY, 2005, 23 (08) : 1076 - 1080
  • [22] Synthesis of Secondary Amines by Iron-Catalyzed Reductive Amination
    Enthaler, Stephan
    CHEMCATCHEM, 2010, 2 (11) : 1411 - 1415
  • [23] Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes
    Ilies, Laurean
    Arslanoglu, Yasin
    Matsubara, Tatsuaki
    Nakamura, Eiichi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1327 - 1329
  • [24] Highly Selective Iron-Catalyzed Synthesis of Alkenes by the Reduction of Alkynes
    Enthaler, Stephan
    Haberberger, Michael
    Irran, Elisabeth
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (06) : 1613 - 1623
  • [25] Iron-Catalyzed Reaction of Urea with Alcohols and Amines: A Safe Alternative for the Synthesis of Primary Carbamates
    Pena-Lopez, Miguel
    Neumann, Helfried
    Beller, Matthias
    CHEMSUSCHEM, 2016, 9 (16) : 2233 - 2238
  • [26] Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
    Rohlmann, Renate
    Stopka, Tobias
    Richter, Heinrich
    Mancheno, Olga Garcia
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 6050 - 6064
  • [27] Sequential catalytic process:: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynes
    Xiao, Fengping
    Chen, Yulin
    Liu, Yu
    Wang, Jianbo
    TETRAHEDRON, 2008, 64 (12) : 2755 - 2761
  • [28] Iron-Catalyzed Oxidative Monoarylation of Primary Amines with Organozinc Reagents
    Nakamura, Yuki
    Ilies, Laurean
    Nakamura, Eiichi
    ORGANIC LETTERS, 2011, 13 (22) : 5998 - 6001
  • [29] Iron(III)-Catalyzed and Air-Mediated Tandem Reaction of Aldehydes, Alkynes and Amines: An Efficient Approach to Substituted Quinolines
    Cao, Ke
    Zhang, Fu-Min
    Tu, Yong-Qiang
    Zhuo, Xiao-Tao
    Fan, Chun-An
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) : 6332 - 6334
  • [30] Iron-Catalyzed Synthesis of (E)-β-Vinylsilanes via a Regio- and Stereoselective Hydrosilylation from Terminal Alkynes
    Liu, Zhi-Kai
    Zhang, Guo-Liang
    Li, Ding-Chang
    Yang, Ying
    Chen, Li
    Zhan, Zhuang-Ping
    SYNLETT, 2019, 30 (02) : 235 - 239