Sonochemical synthesis of methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones using SnII-montmorillonite

被引:44
作者
Ahmadzadeh, Majid [1 ]
Zarnegar, Zohre [1 ]
Safari, Javad [1 ]
机构
[1] Univ Kashan, Coll Chem & Biochem, Dept Organ Chem, Lab Organ Cpds Res, Kashan, Iran
关键词
Isoxazoles; ultrasound irradiation; montmorillonite K10; heterogeneous catalyst; SnCl2; ONE-POT SYNTHESIS; GREEN SYNTHESIS; 3-COMPONENT SYNTHESIS; RECYCLABLE CATALYST; EFFICIENT SYNTHESIS; SODIUM BENZOATE; DERIVATIVES; ISOXAZOLES; AMINE; FACILE;
D O I
10.1080/17518253.2018.1434564
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tin exchanged montmorillonite K10 (Sn-II-Mont K10) was prepared by ion exchange between SnCl2 and montmorillonite K10. The Sn-II-Mont K10 was characterized by X-ray diffraction, scanning electron microscope and energy-dispersive X-ray spectroscopy. The synthesized Sn-II-Mont K10 was used as a recoverable solid catalyst for synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones via one-pot multicomponent cyclocondensation of hydroxylamine hydrochloride, ethyl acetoacetate and benzaldehyde derivatives in water under ultrasound irradiations. The yields of products were obtained 87-96%. The remarkable advantages of this method are a low-cost and eco-friendliness catalyst, rapid completion of the reactions, and avoidance of using organic solvents, excellent yield and mild conditions. [GRAPHICS] .
引用
收藏
页码:78 / 85
页数:8
相关论文
共 46 条
  • [1] Synthesis of pyrrolidinone derivatives from aniline, an aldehyde and diethyl acetylenedicarboxylate in an ethanolic citric acid solution under ultrasound irradiation
    Ahankar, Hamideh
    Ramazani, Ali
    Slepokura, Katarzyna
    Lis, Tadeusz
    Joo, Sang Woo
    [J]. GREEN CHEMISTRY, 2016, 18 (12) : 3582 - 3593
  • [2] Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst
    Brahmachari, Goutam
    Banerjee, Bubun
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (03): : 411 - 422
  • [3] MOSSBAUER SPECTROSCOPIC AND THERMOGRAVIMETRIC STUDIES OF TIN-CLAY COMPLEXES
    BREEN, C
    MOLLOY, KC
    QUILL, K
    [J]. CLAY MINERALS, 1992, 27 (04) : 445 - 455
  • [4] An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium
    Chavan, Abhijit P.
    Pinjari, Avinash B.
    Mhaske, Pravin C.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1911 - 1915
  • [5] Fardood S.T., 2017, APPL ORGANO IN PRESS, DOI [10.1002/ aoc. 3823, DOI 10.1002/A0C.3823]
  • [6] Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe3O4 MNPs in a water/PEG300 system
    Hasanpour, Zeinab
    Maleki, Aziz
    Hosseini, Morteza
    Gorgannezhad, Lena
    Nejadshafiee, Vajihe
    Ramazani, Ali
    Haririan, Ismaeil
    Shafiee, Abbas
    Khoobi, Mehdi
    [J]. TURKISH JOURNAL OF CHEMISTRY, 2017, 41 (02) : 294 - +
  • [7] Synthesis and antibacterial activity of new carbapenems containing isoxazole moiety
    Kang, YK
    Shin, KJ
    Yoo, KH
    Seo, KJ
    Hong, CY
    Lee, CS
    Park, SY
    Kim, DJ
    Park, SW
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (02) : 95 - 99
  • [8] KANO H, 1967, J MED CHEM, V10, P411
  • [9] Karabasanagouda T, 2009, INDIAN J CHEM B, V48, P430
  • [10] One-pot synthesis of 4H-benzo[b]pyrans and dihydropyrano[c]chromenes using inorganic-organic hybrid magnetic nanocatalyst in water
    Khoobi, Mehdi
    Ma'mani, Leila
    Rezazadeh, Faezeh
    Zareie, Zeinab
    Forournadi, Alireza
    Ramazani, Ali
    Shafiee, Abbas
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 359 : 74 - 80