Three-Component Condensation for the Construction of Novel Spirooxindoles

被引:3
|
作者
Ji, Fei [1 ]
Sun, Mu [1 ]
Lv, Mei-fang [1 ]
Yi, Wen-bin [1 ]
Cai, Chun [1 ]
机构
[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 03期
关键词
multicomponent reaction; spirooxindoles; 3+2] cycloaddition; CuAAC reaction; triazoles; AROMATIC CARBOXYLIC-ACIDS; ALKYL ISOCYANIDES; ONE-POT; DIMETHYL ACETYLENEDICARBOXYLATE; DIALKYL ACETYLENEDICARBOXYLATES; STEREOSELECTIVE-SYNTHESIS; SPIROCYCLIC OXINDOLES; ACETYLENIC ESTERS; TERMINAL ALKYNES; FACILE SYNTHESIS;
D O I
10.1055/s-0032-1316836
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new route for the synthesis of novel spirooxindoles from isocyanides, dialkyl acetylenedicarboxylates, and N-substituted isatylidene derivatives through [3+2] cycloaddition has been developed. This method has several advantages, such as high regioselectivity, high yields, readily available starting materials, and one-pot operations. The synthetic alkyne-containing spirooxindoles could also be used in the selective synthesis of triazole-containing spirocyclic compounds using a copper azide-alkyne cycloaddition (CuAAC) reaction.
引用
收藏
页码:375 / 381
页数:7
相关论文
共 50 条
  • [1] Stereoselective Construction of Complex Spirooxindoles via Bisthiourea Catalyzed Three-Component Reactions
    Zhang, Lin-Lin
    Zhang, Ji-Wei
    Xiang, Shao-Hua
    Guo, Zhen
    Tan, Bin
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) : 1182 - 1186
  • [2] Diastereoselective construction of carbazole-based spirooxindoles via the Levy three-component reaction
    Zhan, Shao-Cong
    Sun, Jing
    Liu, Ru-Zhang
    Yan, Chao-Guo
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (01) : 163 - 168
  • [3] Multicomponent Reaction Discovery: Three-Component Synthesis of Spirooxindoles
    Liang, Bo
    Kalidindi, Srinivas
    Porco, John A., Jr.
    Stephenson, Corey R. J.
    [J]. ORGANIC LETTERS, 2010, 12 (03) : 572 - 575
  • [5] A library of spirooxindoles based on a stereoselective three-component coupling reaction
    Lo, MMC
    Neumann, CS
    Nagayama, S
    Perlstein, EO
    Schreiber, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) : 16077 - 16086
  • [6] Iodine-promoted three-component reaction for the synthesis of spirooxindoles
    Zhang, Min
    Yang, Wenbo
    Qian, Min
    Zhao, Ting
    Yang, Liuqing
    Zhu, Chunyin
    [J]. TETRAHEDRON, 2018, 74 (09) : 955 - 961
  • [7] A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium
    Zhu, Song-Lei
    Ji, Shun-Jun
    Zhang, Yong
    [J]. TETRAHEDRON, 2007, 63 (38) : 9365 - 9372
  • [8] Three-component condensation in the synthesis of substituted tetrahydropyridinethiolates
    K. A. Frolov
    V. V. Dotsenko
    S. G. Krivokolysko
    V. P. Litvinov
    [J]. Russian Chemical Bulletin, 2005, 54 : 1335 - 1336
  • [9] Three-component condensation in the synthesis of substituted tetrahydropyridinethiolates
    Frolov, KA
    Dotsenko, VV
    Krivokolysko, SG
    Litvinov, VP
    [J]. RUSSIAN CHEMICAL BULLETIN, 2005, 54 (05) : 1335 - 1336
  • [10] Unexpected preparation of (Z)-chloromethyleneketals and their sulfur analogues by a novel three-component condensation
    Schevenels, Florian
    Marko, Istvan E.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (11) : 3287 - 3289