Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael-Michael addition

被引:4
|
作者
Palanimuthu, Arunan [2 ]
Chen, Chinpiao [1 ,2 ]
Lee, Gene-Hsian [3 ]
机构
[1] Tzu Chi Univ Sci & Technol, Dept Nursing, Hualien 970, Taiwan
[2] Natl Dong Hwa Univ, Dept Chem, Soufeng, Hualien 974, Taiwan
[3] Natl Taiwan Univ, Coll Sci, Instrumentat Ctr, Taipei 106, Taiwan
关键词
CONSTRUCTION; INHIBITORS; ACID; EFFICIENT; DESIGN; SITE;
D O I
10.1039/d0ra01264e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael-Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds.
引用
收藏
页码:13591 / 13600
页数:10
相关论文
共 50 条
  • [1] Organocatalytic Enantioselective Cascade Aza-Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines
    Yang, Wen
    He, Hai-Xiao
    Gao, Yu
    Du, Da-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3670 - 3678
  • [2] Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines
    Yang, Wen
    Du, Da-Ming
    CHEMICAL COMMUNICATIONS, 2013, 49 (78) : 8842 - 8844
  • [3] Catalytic Asymmetric Aza-Michael-Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Aminobenzopyrans
    Wang, Xu-Fan
    An, Jing
    Zhang, Xiao-Xiao
    Tan, Fen
    Chen, Jia-Rong
    Xiao, Wen-Jing
    ORGANIC LETTERS, 2011, 13 (04) : 808 - 811
  • [4] Organocatalyzed Cascade Aza-Michael/Michael Addition for the Asymmetric Construction of Highly Functionalized Spiropyrazolone Tetrahydroquinolines
    Li, Jun-Hua
    Du, Da-Ming
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (11) : 3278 - 3286
  • [5] Highly stereoselective construction of tetrahydroquinolines via cascade aza-Michael-Michael reaction: Formal [4+2] cycloaddition of β,γ-unsaturated α-ketoesters with 2-aminochalcones
    Duan, Cong
    Yao, Yongqi
    Ye, Ling
    Shi, Zhichuan
    Zhao, Zhigang
    Li, Xuefeng
    TETRAHEDRON, 2018, 74 (50) : 7179 - 7185
  • [6] Organocatalytic Aza-Michael-Michael Cascade Reactions: A Flexible Approach to 2,3,4-Trisubstituted Tetrahydroquinolines
    Jia, Zhen-Xin
    Luo, Yong-Chun
    Wang, Yao
    Chen, Liang
    Xu, Peng-Fei
    Wang, Binghe
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (41) : 12958 - 12961
  • [7] Organocatalyzed aza-Michael-Michael cascade reactions to construct spirooxindole tetrahydroquinolines with all-carbon chiral centers
    Huang, You-ming
    Zheng, Chang-wu
    Zhao, Gang
    RSC ADVANCES, 2013, 3 (38): : 16999 - 17002
  • [8] Synthesis of Multisubstituted Tetrahydroquinolines through Aza-Michael/Michael Addition Catalyzed by Quaternary Ammonium Salt
    Zhang, Li
    Li, Yajun
    Yuan, Yafen
    Zhang, Bin
    Gao, Yuan
    Wu, Yongming
    Song, Liping
    SYNLETT, 2014, 25 (12) : 1781 - 1785
  • [9] Highly Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via Organocatalytic Michael/Aza-Henry Tandem Reactions
    Jia, Zhen-Xin
    Luo, Yong-Chun
    Xu, Peng-Fei
    ORGANIC LETTERS, 2011, 13 (05) : 832 - 835
  • [10] Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α, β-unsaturated ketones: construction of chiral functionalized tetrahydroquinolines
    Kim, Shinae
    Kang, Ki-Tae
    Kim, Sung-Gon
    TETRAHEDRON, 2014, 70 (34) : 5114 - 5121