One-pot multicomponent green synthesis of novel series of 4-hydroxy-2-pyridone-fused spiropyrans catalyzed by acetic acid

被引:2
|
作者
Kamali, Mahmood [1 ,2 ]
Ebrahimi, Asadollah [1 ]
机构
[1] Kharazmi Univ, Fac Chem, Dept Organ & Polymer Chem, Tehran, Iran
[2] Kharazmi Univ, Fac Chem, Dept Organ & Polymer Chem, Tehran 1571914911, Iran
关键词
4-Hydroxy-pyridine-2-one; isatin; multicomponent reaction; ninhydrin; spiropyran; 2-AMINO-4H-CHROMENE DERIVATIVES; 3-COMPONENT SYNTHESIS; NATURAL-PRODUCTS; EFFICIENT; DISCOVERY; FACILE; 2-AMINO-4H-PYRANS; SPIROOXINDOLES; APOPTOSIS; DRUGS;
D O I
10.1080/00397911.2023.2230504
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot multicomponent reaction is reported for synthesizing a novel series 4-hydroxy-2-pyridone-fused spiropyran through the reaction of 4-hydroxy-6-methylpyridine-2-ones alkaloids, malononitrile or ethyl cyanoacetate, and ninhydrin or isatin derivatives. The optimized conditions for this reaction were obtained in ethanol solvent, acetic acid as catalyst, ambient temperature (for ninhydrin) or 70 & DEG;C (for isatin), and 8 hr reaction time. Mild and safe conditions, easy work-up and separation, high to excellent yields, and eco-compatibility are the main advantages of this synthesis for affording potentially bio-effective novel products.
引用
收藏
页码:1439 / 1450
页数:12
相关论文
共 50 条
  • [1] Green, One-Pot, Multicomponent Synthesis of Fused-Ring 2-Aminothiazoles
    Anwar, Siddique
    Paul, Satya B.
    Majumdar, K. C.
    Choudhury, Sudip
    SYNTHETIC COMMUNICATIONS, 2014, 44 (22) : 3304 - 3313
  • [2] Heteropolyacid-Catalyzed One-Pot Synthesis of 2-Pyridone Derivatives
    Samzadeh-Kermani, Alireza
    SYNLETT, 2016, 27 (03) : 461 - 464
  • [3] Green synthesis of novel cyclopentapyridines: One-pot multicomponent reactions of vinilydene Meldrum's acid
    Amiri, Somayeh Soleimani
    Azizi, Zahra
    Hossaini, Zinatossadat
    Jouladehroodbar, Hadi
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (09) : 1379 - 1386
  • [4] Trypsin-Catalyzed One-Pot Multicomponent Synthesis of 4-Thiazolidinones
    Hui Zheng
    Yi-Jia Mei
    Kui Du
    Qiao-Yue Shi
    Peng-Fei Zhang
    Catalysis Letters, 2013, 143 : 298 - 301
  • [5] Trypsin-Catalyzed One-Pot Multicomponent Synthesis of 4-Thiazolidinones
    Zheng, Hui
    Mei, Yi-Jia
    Du, Kui
    Shi, Qiao-Yue
    Zhang, Peng-Fei
    CATALYSIS LETTERS, 2013, 143 (03) : 298 - 301
  • [6] One-pot Biginelli synthesis of novel series of 2-oxo/thioxo/imino-1,2,3,4-tetrahydropyrimidine based on 4-hydroxy-2-pyridone
    Kamali, Mahmood
    Mohammadzadeh, Saeedeh
    CHEMICAL PAPERS, 2023, 77 (09) : 4943 - 4952
  • [7] One-Pot Synthesis of Anthraquinone Catalyzed by Microwave Acetic Acid Modified Hβ Zeolite
    Wang, Teng
    Yu, Hailong
    Bian, Bing
    Liu, Yue
    Liu, Shiwei
    Yu, Shitao
    Wang, Zhiping
    CATALYSIS LETTERS, 2020, 150 (10) : 3007 - 3016
  • [8] One-Pot Synthesis of Anthraquinone Catalyzed by Microwave Acetic Acid Modified Hβ Zeolite
    Teng Wang
    Hailong Yu
    Bing Bian
    Yue Liu
    Shiwei Liu
    Shitao Yu
    Zhiping Wang
    Catalysis Letters, 2020, 150 : 3007 - 3016
  • [9] One-pot Biginelli synthesis of novel series of 2-oxo/thioxo/imino-1,2,3,4-tetrahydropyrimidine based on 4-hydroxy-2-pyridone
    Mahmood Kamali
    Saeedeh Mohammadzadeh
    Chemical Papers, 2023, 77 : 4943 - 4952
  • [10] One-pot Synthesis of Highly Functionalized Tetrahydropyridines: A Camphoresulfonic Acid Catalyzed Multicomponent Reaction
    Bharti, Ruchi
    Parvin, Tasneem
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1806 - 1811