A water mediated multicomponent reaction for the synthesis of novel spirooxindole derivatives and their antifungal activity

被引:0
|
作者
Zhang, Min [1 ]
Shi, Liang [1 ]
Chen, Li [1 ]
Liu, Zhengyu [1 ]
Zhao, Ting [1 ]
Zhu, Chunyin [1 ]
Yang, Liuqing [1 ]
机构
[1] Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Peoples R China
基金
中国国家自然科学基金;
关键词
ORGANIC-REACTIONS; SCAFFOLD;
D O I
10.1039/d4ob00256c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A water mediated three-component reaction of isatin, 4-aminocoumarin, and 1,3-cyclodicarbonyl compounds is reported for the synthesis of spiro[chromeno[4,3-b]cyclopenta[e]pyridine-7,3 '-indoline]trione and the spiro[chromeno[4,3-b]quinoline 7,3 '-indoline]trione. Up to 27 different spirooxindole derivatives were synthesized by this method. The bioactivity of these spirooxindole derivatives was evaluated and they were found to show antifungal activity against Cercospora arachidicola, Physalospora piricola, Rhizoctonia cerealis, and Fusarium moniliforme. A total of 27 novel spirooxindoles were synthesized through a water mediated three-component reaction of isatin, 4-aminocoumarin, and 1,3-cyclodicarbonyl compounds. Several compounds showed excellent antifungal activity against Physalospora piricola.
引用
收藏
页码:3459 / 3467
页数:9
相关论文
共 50 条
  • [1] Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity
    Bhaskar, Gangaru
    Arun, Yuvaraj
    Balachandran, Chandrasekar
    Saikumar, Chandrasekara
    Perumal, Paramasivan T.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 : 79 - 91
  • [2] Synthesis and antifungal activities of novel polyheterocyclic spirooxindole derivatives
    Wu, Jia-Shou
    Zhang, Xue
    Zhang, Ying-Lao
    Xie, Jian-Wu
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4967 - 4975
  • [3] Electrocatalytic Multicomponent Reaction for Synthesis of Nanoparticles of Spirooxindole Derivatives from Isatins, Malononitrile, and Dimedone
    Darvish, Zahra Mohammad
    Mirza, Behrooz
    Makarem, Somayeh
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) : 1763 - 1766
  • [4] A rapid and high efficient microwave promoted multicomponent domino reaction for the synthesis of spirooxindole derivatives
    Ghahremanzadeh, Ramin
    Rashid, Zahra
    Zarnani, Amir-Hassan
    Naeimi, Hossein
    [J]. JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2014, 20 (06) : 4076 - 4084
  • [5] Oligosaccharides as Green Catalyst for One-Pot Multicomponent Synthesis of Spirooxindole Derivatives in Water
    Jha, Anand Mohan
    Jha, Nidhi
    [J]. INTERNATIONAL JOURNAL OF LIFE SCIENCE AND PHARMA RESEARCH, 2020, 10 (02): : L88 - L93
  • [6] Ammonium acetate mediated simple, rapid, and one-pot multicomponent synthesis of spirooxindole derivatives
    Raheja, Barkha K.
    Dalal, Dipak S.
    [J]. SYNTHETIC COMMUNICATIONS, 2023, 53 (11) : 808 - 822
  • [7] Bronsted or Lewis Acid Initiated Multicomponent Cascade Reaction: Diastereoselective Synthesis of Imidazolidinyl Spirooxindole Derivatives
    Zhang, Jun-Qi
    Qi, Zheng-Hang
    Yin, Shao-Jie
    Li, Hai-Yan
    Wang, Yong
    Wang, Xing-Wang
    [J]. CHEMCATCHEM, 2016, 8 (17) : 2797 - 2807
  • [8] Efficient Multicomponent Synthesis of Spirooxindole Derivatives Catalyzed by Copper Triflate
    Wu, Chunlei
    Liu, Jian
    Kui, Du
    Lemao, Yu
    Yingjie, Xu
    Luo, Xiang
    Meiyang, Xi
    Shen, Runpu
    [J]. POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (01) : 277 - 289
  • [9] Synthesis and Antifungal Activity of Novel Triazole Derivatives
    Yan, Yongzheng
    Yu, Shichong
    Chai, Xiaoyun
    Hu, Honggang
    Wu, Qiuye
    [J]. ARCHIVES OF PHARMACAL RESEARCH, 2011, 34 (10) : 1649 - 1656
  • [10] Synthesis and antifungal activity of novel triazole derivatives
    Sun Qing-Yan
    Cao Yong-Bing
    Xu Jian-Ming
    Zhang Wan-Nian
    Zhang Jun
    Wu Qiu-Ye
    Zhang Da-Zhi
    Jiang Yuan-Ying
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2007, 28 (09): : 1707 - 1709