Sulfated polyborate catalyzed expeditious and efficient three-component synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5 (4H)-ones

被引：65
|
作者：
Patil, Manisha S. [1 ]
Mudaliar, Chirag [1 ]
Chaturbhuj, Ganesh U. [1 ]
机构：
[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 33期
关键词：
Sulfated polyborate; Isoxazole; Aldehyde; Ethyl acetoacetate; Hydroxylamine hydrochloride; ONE-POT SYNTHESIS; AQUEOUS-MEDIA; 3-METHYL-4-ARYLMETHYLENE-ISOXAZOL-5(4H)-ONES; INHIBITORS; MILD; ACID;
D O I：
10.1016/j.tetlet.2017.07.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rapid and highly efficient methodology for the synthesis of 3-methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones has been developed using sulfated polyborate as a catalyst. The multicomponent reaction of an aromatic/heterocyclic aldehyde, hydroxylamine hydrochloride, and ethyl acetoacetate under a solvent free condition at 80 degrees C is described. This protocol has promising features for the reaction response such as shorter reaction time, easy work-up, ease of separation of pure product with high yields and simplicity in the experimental procedure. The products have been obtained in high yields (80-90%) and convenient reaction time (15-30 min). The method is operationally simple and eco-friendly. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3256 / 3261
页数：6
相关论文
共 50 条
  • [1] Na2S2O3 Catalyzed Three-component Synthesis and Anti-bacterial Activity of 3-methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones
    Bi, Yongchang
    Wang, Jingjun
    Bian, Xingyu
    Chen, Mingyue
    Zhu, Guangyuan
    Zhang, Yumin
    Gu, Qiang
    CHEMISTRY & BIODIVERSITY, 2024, 21 (04)
  • [2] Sulfonated Graphene-Oxide as Metal-Free Efficient Carbocatalyst for the Synthesis of 3-Methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones and Substituted Pyrazole
    Basak, Puja
    Dey, Sourav
    Ghosh, Pranab
    CHEMISTRYSELECT, 2020, 5 (02): : 626 - 636
  • [3] Sonochemical synthesis of methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones using SnII-montmorillonite
    Ahmadzadeh, Majid
    Zarnegar, Zohre
    Safari, Javad
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2018, 11 (02) : 78 - 85
  • [4] One-Pot Multicomponent Synthesis of 3-Methyl-4-(Hetero)Arylmethylene Isoxazole-5(4H)-Ones Using Guanidine Hydrochloride as the Catalyst under Aqueous Conditions
    Barkule, Angad B.
    Gadkari, Yatin U.
    Telvekar, Vikas N.
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (09) : 5870 - 5881
  • [5] Concentrated Solar Radiation Aided Green Approach for Preparative Scale and Solvent-Free Synthesis of 3-Methyl-4-(hetero)arylmethylene Isoxazole-5(4H)-ones
    Gadkari, Yatin U.
    Jadhav, Nilesh L.
    Hatvate, Navnath T.
    Telvekar, Vikas N.
    CHEMISTRYSELECT, 2020, 5 (39): : 12320 - 12323
  • [6] Synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones by visible light in aqueous ethanol
    Saikh, Forid
    Das, Jhantu
    Ghosh, Somnath
    TETRAHEDRON LETTERS, 2013, 54 (35) : 4679 - 4682
  • [7] Sonochemical synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones by amine-modified montmorillonite nanoclay
    Safari, Javad
    Ahmadzadeh, Majid
    Zarnegar, Zohre
    CATALYSIS COMMUNICATIONS, 2016, 86 : 91 - 95
  • [8] Synthesis, Computational, Anticancer, and Electrochemical Behavior Studies of 3-Methyl-4-(hetero)aryl Methylene Isoxazole-5(4H)-One
    Mane, Radhika
    Yaraguppi, Deepak A.
    Chandrakala, K. B.
    Kamanna, Kantharaju
    CHEMISTRYSELECT, 2024, 9 (33):
  • [9] Phthalimide-N-oxyl salts: efficient organocatalysts for facile synthesis of (Z)-3-methyl-4-(arylmethylene)-isoxazole-5(4H)-one derivatives in water
    Mohammad G. Dekamin
    S. Zahra Peyman
    Monatshefte für Chemie - Chemical Monthly, 2016, 147 : 445 - 450
  • [10] ONE-POT THREE-COMPONENT SYNTHESIS OF 3-METHYL-4-ARYLMETHYLENE-ISOXAZOL-5(4H)-ONES CATALYZED BY SODIUM SULFIDE
    Liu, Qing
    Hou, Xianming
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (04) : 448 - 453
12345