Ultrasound-assisted synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones by novel core-shell bio-based nanocatalyst anchoring sulfonated L-histidine on magnetized silica (SO3H-L-His@SiO2-nano Fe3O4)

被引:11
|
作者
Nikoofar, Kobra [1 ]
Peyrovebaghi, Seyedeh S. [1 ]
机构
[1] Alzahra Univ, Fac Phys & Chem, Dept Chem, Tehran, Iran
关键词
3-phenacylidenox; indole; core-shell nanostructure; nanomagnetite; tetrahydro-1H-indolyl-indolin-2-ones; tryptamine; ultrasound irradiation; ONE-POT; NANOPARTICLES; DERIVATIVES; EFFICIENT; CATALYST; ARYLAMINES; INHIBITORS; CHEMISTRY; OXINDOLE; SCAFFOLD;
D O I
10.1002/jccs.201900365
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones is reported via a one-pot three-component reaction of 3-phenacylidenoxindoles, tryptamine, and dimedone under ultrasound irradiation using a newly prepared core-shell nanostructure. The utilized nanocatalyst is obtained by anchoring sulfonated L-histidine amino acid shell, as the bio part, on silica-nanomagnetite core (SO3H-L-His@SiO2-nano Fe3O4) and characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy (H-1 NMR), field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric/differential thermal analysis, vibrating sample magnetometer measurements, transmission electron microscopy, and back-titration. The protocol contains several advantages, such as relatively short reaction times, simple work-up procedure by separation of the catalyst with an external magnet, the use of economical and environmentally friendly ultrasonic waves, and reusability and recoverability of the core-shell nano-promoter for three runs without significant activity loss.
引用
收藏
页码:1303 / 1313
页数:11
相关论文
共 18 条
  • [1] Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1H-Indol-3-yl) ethyl]-4,5,6,7-tetrahydro-1H- indol-3-yl} indolin-2-ones
    Jiang, Yan-Hong
    Yan, Chao-Guo
    SYNTHESIS-STUTTGART, 2016, 48 (18): : 3057 - 3064
  • [2] Multi-component Synthesis of 3-{3-[2-(1H-Indol-3-yl) ethyl]}-2,3-dihydro-2-(aryliminothiazol-4-yl)-2H-chromen-2-ones
    Aychiluhim, Tewodros Birhanu
    Rao, Vedula Rajeswar
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2014, 46 (01) : 66 - 75
  • [3] Ultrasound-assisted three-component synthesis of 3-(5-amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones in water
    Khorrami, Afshin Rajabi
    Faraji, Fereshteh
    Bazgir, Ayoob
    ULTRASONICS SONOCHEMISTRY, 2010, 17 (03) : 587 - 591
  • [4] Synthesis, Characterization, and Antioxidant Properties of Novel 1-(4-Aryl-1,3-thiazol-2-yl)-2-{[1-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methylidene}hydrazines
    Durgeswari, L. K.
    Ganta, Ravi Kumar
    Murthy, Y. L. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (09) : 1552 - 1558
  • [5] SYNTHESIS AND SCREENING OF 2-(2-(3-(4-FORMYL-TETRAHYDRO-2-PHENYLTHIOPHENE- 3-YL)-1H-INDOL-1-YL) ACETAMIDO)-N-1-(2-OXO-1( PIPERIDIN-1-YL) METHYL) INDOLIN-3-YLIDENE) METHYLENE) PROPANE HYDRAZINE
    Muralikrishna, S.
    Reddy, P. Raveendra
    Ravindranath, L. K.
    Rao, P. Jagadeeswara
    HETEROCYCLIC LETTERS, 2014, 4 (04): : 549 - 558
  • [6] One-Pot, Three-Component Synthesis of 3-(5-Amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones
    Ahadi, Somayeh
    Mirzaei, Peiman
    Bazgir, Ayoob
    SYNTHETIC COMMUNICATIONS, 2010, 40 (08) : 1224 - 1230
  • [7] Iodine-catalyzed conjugate addition of indoles onto en-1,4-dione: A novel synthesis of 3-(1-(1H-indol-3-yl)-2-oxo-2-phenylethyl)indolin-2-ones as antibacterial and antifungal agents
    Reddy, B. V. Subba
    Rajeswari, N.
    Sarangapani, M.
    Reddy, G. Roopa
    Madan, Ch.
    Kumar, K. Pranay
    Rao, M. Srinivasa
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (21) : 6510 - 6514
  • [8] Synthesis and Antibacterial Activity of 5-Aryl-4-[hydroxy(4-chlorophenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,3-diones
    Gein, V. L.
    Kazantseva, M. I.
    Varkentin, L. I.
    Zamaraeva, T. M.
    Yankin, A. N.
    Beletskii, E. V.
    Novikova, V. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2020, 90 (08) : 1426 - 1431
  • [9] Indium chloride catalyzed three-component reaction for the synthesis of 2-((oxoindolin-3-yl)-4,5,6,7-tetrahydro-1H-indol-1-yl)benzamides
    Jiang, Yan-Hong
    Yan, Chao-Guo
    RSC ADVANCES, 2016, 6 (48) : 42173 - 42179
  • [10] Microwave-assisted synthesis and antibacterial activity of derivatives of 3-[1-(4-fluorobenzyl)-1H-indol-3-yl]-5-(4-fluorobenzylthio)-4H-1,2,4-triazol-4-amine
    Peng, Yong-Le
    Liu, Xing-Li
    Wang, Xiao-Hong
    Zhao, Zhi-Gang
    CHEMICAL PAPERS, 2014, 68 (03) : 401 - 408