CoFe2O4@SiO2@APTES@HO-PBA@Cu(OAc)2: A highly efficient and recyclable nanocatalyst for one-pot synthesis of multifunctional 1,5-benzodiazepines via three-component domino reaction

被引:8
作者
Wen, T. T. [1 ]
Wang, L. Z. [1 ]
机构
[1] Hebei Normal Univ, Coll Chem & Mat Sci, Hebei Key Lab Organ Funct Mol, Shijiazhuang 050024, Hebei, Peoples R China
基金
中国国家自然科学基金;
关键词
Magnetic nanocatalyst; 1; 5-Benzodiazepines; Domino reaction; Recyclability; BIOLOGICAL EVALUATION; CATALYZED SYNTHESIS; GREEN SYNTHESIS; DERIVATIVES; NANOPARTICLES; INHIBITORS; CELLULOSE; COMPLEX; DESIGN; SERIES;
D O I
10.1016/j.mtchem.2022.101071
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CoFe2O4@SiO2@APTES@HO-PBA@Cu(OAc)2: A magnetic core-shell copper-based nanocatalyst was suc-cessfully prepared. The fabricated nanocatalyst was structurally authenticated using various analytical techniques such as FT-IR, XRD, SEM, TEM, EDS, ICP-AES, TGA/DTA, XPS, BET, and VSM. The highly pro-ficient catalyst proved its dependability for one-pot synthesis of diester/methyl-substituted polycyclic fused 1,5-benzodiazepines via three-component domino reaction of nucleophilic addition and elimina-tion, Michael addition, C-C cross-coupling reactions, and H proton transfer reaction in good to excellent yields. Also, all products were obtained in high TON (up to 17,241) and TOF (up to 4816), which reveals the nanocatalyst has high activity and selectivity in described domino reactions. The suggested mech-anism for one-pot synthesis of diester/methyl-substituted polycyclic fused 1,5-benzodiazepines in the presence of copper-based nanocatalyst was also proposed, respectively. The nanocatalyst can be reused seven times without significant loss of its catalytic efficiency. The easy recovery of the nanocatalyst and reusability, broad substrate scopes, short reaction time, high yields of products, and mild conditions make this protocol practical, environmentally friendly, and economically attractive.(c) 2022 Elsevier Ltd. All rights reserved.
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页数:14
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共 64 条
[1]  
Ahmadzadeh F, 2021, J CHEM SOC PAKISTAN, V43, P456
[2]   One-pot synthesis of 1,5-benzodiazepine-2,3-dicarboxylates via three-component domino reactions in the presence of γ-Fe2O3@SiO2/Ce(OTf)3 [J].
An, Xiaoying ;
Gao, Lei ;
Wang, Mingliang ;
Wu, Haitao ;
Wang, Lanzhi .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (7-8) :806-816
[3]   Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5-Benzodiazepine Derivatives as Potential Antimicrobial Agents [J].
An, Ying-shuang ;
Hao, Zhen-fang ;
Zhang, Xiu-jun ;
Wang, Lan-zhi .
CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 88 (01) :110-121
[4]   A sustainable gateway to access 1,8-dioxo-octahydroxanthene scaffolds via a surface-engineered halloysite-based magnetically responsive catalyst [J].
Arora, Bhavya ;
Sharma, Shivani ;
Dutta, Sriparna ;
Sharma, Aditi ;
Yadav, Sneha ;
Rana, Pooja ;
Sharma, R. K. .
NEW JOURNAL OF CHEMISTRY, 2022, 46 (11) :5405-5418
[5]   Recent advances in synthesis and medicinal chemistry of benzodiazepines [J].
Arora, Nidhi ;
Dhiman, Prashant ;
Kumar, Shubham ;
Singh, Gurpreet ;
Monga, Vikramdeep .
BIOORGANIC CHEMISTRY, 2020, 97
[6]   Multicomponent and One-pot Syntheses of Quinoxalines [J].
Biesen, Lukas ;
Mueller, Thomas J. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (04) :980-1006
[7]   Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action [J].
Caiana, Elizeu C. ;
de Veras, Bruno O. ;
de Souza, Antonia L. ;
Queiroz, Neide .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2021, 32 (03) :626-637
[8]   Palladium-Catalyzed Benzodiazepines Synthesis [J].
Christodoulou, Michael S. ;
Beccalli, Egle M. ;
Giofre, Sabrina .
CATALYSTS, 2020, 10 (06)
[9]   Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives [J].
Curini, M ;
Epifano, F ;
Marcotullio, MC ;
Rosati, O .
TETRAHEDRON LETTERS, 2001, 42 (18) :3193-3195
[10]   Ionic Liquid-Assisted Preparation of Co3O4 Nanosheets as a New and Efficient Catalyst for Green Synthesis of Various 1,5-Benothiazepine Derivatives in Water [J].
Darband, M. ;
Tahanpesar, E. ;
Sanaeishoar, H. ;
Badri, R. .
RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2021, 94 (12) :1624-1634