Phosphine-Mediated [3+2] Cyclization for the Synthesis of Coumarin-Based CF 3 -Containing Furanones

被引:1
|
作者
Gan, Wenhao [1 ]
Fu, Junfeng [1 ]
Zhou, Zhixiang [1 ]
Cao, Sheng [1 ]
Zhang, Zhipeng [1 ]
Wang, Yongjiang [1 ]
Han, Xiaoyu [1 ]
机构
[1] Zhejiang Univ Sci & Technol, Sch Biol & Chem Engn, Zhejiang Prov Key Lab Chem & Biol Proc Technol Far, Hangzhou 310023, Peoples R China
关键词
phosphine; cyclization; coumarin; furanone; ENE-YNE-KETONES; DOMINO REACTION; 4+2 ANNULATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; FUNCTIONALIZED COUMARIN; CATALYZED SYNTHESIS; DERIVATIVES; CYCLOADDITION; ALLENES;
D O I
10.1055/s-0042-1751434
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tertiary phosphine-mediated [3+2] cyclization reaction of ynones with fluorinated coumarin derivatives has been developed to give a series of coumarin-based CF3-containing furanones in moderate to good yields under mild reaction conditions. Preliminary investigation into their antitumor activities is also presented.
引用
收藏
页码:1587 / 1592
页数:6
相关论文
共 50 条
  • [21] Phosphine-Catalyzed Annulations Based on [3+3] and [3+2] Trapping of Ketene Intermediates with Thioamides
    Wang, Yu-Hao
    Zhao, Zhen-Ni
    Kalita, Subarna Jyoti
    Huang, Yi-Yong
    ORGANIC LETTERS, 2021, 23 (21) : 8147 - 8152
  • [22] Efficient synthesis of functionalized furans and benzofurans based on a '[3+2] cyclization/oxidation' strategy
    Bellur, E
    Freifeld, I
    Langer, P
    TETRAHEDRON LETTERS, 2005, 46 (13) : 2185 - 2187
  • [23] Phosphine-catalyzed [3+2] cycloaddition of allenoates with trifluoromethylketones: synthesis of dihydrofurans and tetrahydrofurans
    Wang, Tong
    Ye, Song
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5260 - 5265
  • [24] Enantioselective Phosphine-Catalyzed Trimerization of γ-Aryl-3-butynoates via Isomerization/[3+2] Cyclization/Michael Addition Cascade
    Gao, Yujia
    Zhang, Juan
    Shan, Wenyu
    Fei, Weihong
    Yao, Jinzhong
    Yao, Weijun
    ORGANIC LETTERS, 2021, 23 (16) : 6377 - 6381
  • [25] Silver-Mediated Radical Trifluoromethylthiolation Cyclization: Synthesis of CF3S-Containing Benzimidazole[2,1-a]isoquinolines
    Liu Bing
    Wang Zhichuang
    Sun Kai
    Tang Shi
    Wang Xin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (05) : 1387 - 1395
  • [26] Asymmetric [3+2] Cycloaddition of Olefins with Morita-Baylis-Hillman Carbonates Catalyzed by BINOL-Based Bifunctional Phosphine
    Cui, Hai-Lei
    Tang, Xue
    Li, Meng-Fan
    Xu, Xing-Jie
    Shi, Yin
    SYNLETT, 2019, 30 (07) : 845 - 850
  • [27] Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones
    Neel, Mathilde
    Gouin, Jerome
    Voituriez, Arnaud
    Marinetti, Angela
    SYNTHESIS-STUTTGART, 2011, (12): : 2003 - 2009
  • [28] The [3+2] Annulation of CF3-Ketimines by Re Catalysis: Access to CF3-Containing Amino Heterocycles and Polyamides
    Zhang, Saisai
    Liu, Xun-Yong
    Chang, Zhenbang
    Qiao, Xinxin
    Xiong, Heng-Ying
    Zhang, Guangwu
    ISCIENCE, 2020, 23 (11)
  • [29] The asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds via [3+2] cycloaddition
    Li, Boyu
    Liu, Jikun
    Gao, Fengyun
    Sun, Mengmeng
    Guo, Yifei
    Zhou, Yuan
    Wen, Dongwa
    Deng, Yabo
    Chen, Hui
    Wang, Kairong
    Yan, Wenjin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (11) : 2892 - 2895
  • [30] Tf2O-Catalyzed Tandem Cyclization/Trifluoromethylselenolation of Alkynes for Synthesis of CF3Se-Containing Heterocycles
    Zhang, Shangbiao
    Gao, Yan
    Xiao, Rui
    Li, Yang
    Wang, Yanan
    Yuan, Zheliang
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (41)