Phosphine-Catalyzed [4+1] Annulation of β'-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives

被引：0
|
作者：
Ni, Chunjie [1 ]
Liang, Zhanhang [1 ,3 ]
Xu, Xiaojuan [1 ,3 ]
Yu, Fan [1 ]
Zhao, Yining [1 ]
Chen, Chen [2 ]
机构：
[1] Yancheng Teachers Univ, Sch Pharm, Yancheng 224007, Peoples R China
[2] Tianjin Normal Univ, Coll Chem, Tianjin 300387, Peoples R China
[3] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期
基金：
中国国家自然科学基金;
关键词：
3+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; 2,3-BUTADIENOATES; 2-BUTYNOATES; ITACONIMIDES; FACILE; YLIDES;
D O I：
10.1021/acs.joc.4c02014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A phosphine-catalyzed [4 + 1] annulation of beta'-acetoxy allenoate with alpha-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization of alpha-alkylidene succinimides, resulting in the formation of functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope and yields ranging from moderate to excellent under the optimized conditions. In addition, the biological evaluation indicates that the cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, and HepG2).
引用
收藏
页码：16711 / 16720
页数：10
相关论文
共 50 条
  • [1] Phosphine-catalyzed [5+1] annulation of β'-acetoxy allenoates: straightforward access to tetrahydroquinoline derivatives
    Zhu, Yannan
    Xu, Zhili
    Wang, Yi-Ning
    CHEMICAL COMMUNICATIONS, 2023, 59 (78) : 11712 - 11715
  • [2] Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation
    Han, Xiaoyu
    Yao, Weijun
    Wang, Tianli
    Tan, Yong Ren
    Yan, Ziyu
    Kwiatkowski, Jacek
    Lu, Yixin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5643 - 5647
  • [3] Phosphine-Catalyzed [4+3] Annulation of β′-Acetoxy Allenoates with 1C,3N-Dinucleophiles: Access to Functionalized Azepine Derivatives
    Ni, Chunjie
    Liang, Zhanhang
    Xu, Xiaojuan
    Yu, Fan
    Zhang, Dong
    Chen, Chen
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4784 - 4791
  • [4] Mechanistic studies on phosphine-catalyzed [4+3] annulation of β′-acetoxy allenoate with 1C,3N-dinucleophile
    Yuan, Kui
    Yang, Hao-Ran
    Wang, Yang
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2024, 1241
  • [5] Chiral phosphine-catalyzed asymmetric [4+1] annulation of polar dienes with allylic derivatives: Enantioselective synthesis of substituted cyclopentenes
    Li, Hanyuan
    He, Zhengjie
    TETRAHEDRON LETTERS, 2021, 67
  • [6] Phosphine-catalyzed enantioselective [4+1] annulation of oxindoles with allenic ketones for the construction of spirocyclopentene oxindoles
    Tang, Xiaodong
    Ni, Huanzhen
    Lu, Yixin
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (16) : 4485 - 4489
  • [7] Phosphine-catalysed (4+1) annulations of β′-acetoxy allenoate with β,γ-unsaturated carbonyl compounds
    Zhang, Yueqi
    Wang, Danfeng
    Tong, Xiaofeng
    CHEMICAL COMMUNICATIONS, 2021, 57 (28) : 3488 - 3491
  • [8] Phosphine-Catalyzed [4+1] Annulation of Salicyl Imines with Maleimides and Synthesis of Spiro[benzofuran-2,3′-pyrrolidine] Derivatives
    Yang, Mei
    Cao, Shixuan
    He, Zhengjie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (08) : 2235 - 2242
  • [9] Phosphine-Catalyzed [4+2] Annulation of γ-Substituent Allenoates: Facile Access to Functionalized Spirocyclic Skeletons
    Li, Erqing
    Huang, You
    Liang, Ling
    Xie, Peizhong
    ORGANIC LETTERS, 2013, 15 (12) : 3138 - 3141
  • [10] Phosphine-Catalyzed [4+2] Annulation of Allenoate with Sulfamate-Derived Cyclic 'mines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
    Mao, Biming
    Shi, Wangyu
    Liao, Jianning
    Liu, Honglei
    Zhang, Cheng
    Guo, Hongchao
    ORGANIC LETTERS, 2017, 19 (23) : 6340 - 6343
12345