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
  • [31] Efficient Synthesis of 4-Arylmethylene-3-methylisoxazol-5(4H)-one Derivatives Catalyzed by Malic Acid
    Tahmasabi, Sayed Zakaria
    Kiyani, Hamzeh
    Samimi, Heshmat Allah
    LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (02) : 167 - 174
  • [32] Three-component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)- ones in he Presence of Potassium 2,5-dioxoimidazolidin-1-ide
    Reihani, Neda
    Kiyani, Hamzeh
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (08) : 950 - 962
  • [33] One-pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones Catalyzed by Sodium Benzoate in Aqueous Media: A Green Chemistry Strategy
    Liu, Qing
    Zhang, Ya-Nan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (10) : 3559 - 3560
  • [34] One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation
    Cheng, Qingfang
    Xu, Xingyou
    Wang, Qifa
    Liu, Lisha
    Liu, Wangjun
    Lin, Qiao
    Yang, Xujie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (08) : 1267 - 1271
  • [35] Synthesis and characterization of nanocrystalline hydroxyapatite and its catalytic behavior towards synthesis of 3,4-disubstituted isoxazole-5(4H)-ones in water
    Maleki, Behrooz
    Chahkandi, Mohammad
    Tayebee, Reza
    Kahrobaei, Sepideh
    Alinezhad, Heshmatollah
    Hemmati, Saba
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (10)
  • [36] A Simple and Efficient Protocol for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-Ones Catalyzed by Succinic Acid Using Water as Green Reaction Medium
    Ghogare, Ramesh S.
    Patankar-Jain, Kalpana
    Momin, Sana Amir Hamzah
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (02) : 83 - 87
  • [37] Iodine Catalyzed Highly Efficient One Pot Three Component Synthesis of 4-arylidene-3-methylisoxazol-5 (4H) -one in Aqueous Medium
    Nakkalwar, Srinivas L.
    Patwari, Shivaji B.
    Patel, Mohasim M.
    Jadhav, Vivekanand B.
    CURRENT GREEN CHEMISTRY, 2018, 5 (02) : 121 - 126
  • [38] New eco-friendly procedure for the synthesis of 4-arylmethylene-isoxazol-5(4H)-ones catalyzed by pyridinium p-toluenesulfonate (PPTS) in aqueous medium
    Laroum, Rima
    Debache, Abdelmadjid
    SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1876 - 1882
  • [39] An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium
    Chavan, Abhijit P.
    Pinjari, Avinash B.
    Mhaske, Pravin C.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1911 - 1915
  • [40] Introduction of [2,2'-Bipyridine]-1,1'-Diium Perchlorate as a Novel and Highly Efficient Dicationic Bronsted Acidic Organic Salt for the Synthesis of 3-Methyl-4-Arylmethylene Isoxazole-5(4H)-One Derivatives in Water
    Aleaba, Gilda
    Khedmatgozar Asadi, Shaghayegh
    Daneshvar, Nader
    Shirini, Farhad
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (10) : 7569 - 7581
12345