Synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1h-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives using an engineered copper-based nano-magnetic catalyst (Fe3O4@CQD@Si(OEt)(CH2)3NH@CC@Ad@Cu(OAc)2)

被引:8
作者
Gorji, Atefeh [1 ]
Akbarpour, Tahereh [1 ]
Khazaei, Ardeshir [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan, Hamadan, Iran
关键词
Carbon quantum dots (CQDs); Design of Experiment (DoE); hexahydroquinolines; magnetic nano catalyst; solvent-free reaction; 5-amino-1; 3-diphenyl-1H-pyrazole-4-carbonitrile; 1-aminoalkyl-2-naphthols; ONE-POT SYNTHESIS; SOLVENT-FREE; IONIC LIQUID; RECOVERABLE CATALYST; RECYCLABLE CATALYST; HIGHLY EFFICIENT; GREEN SYNTHESIS; NEW-GENERATION; BETA-NAPHTHOL; MOLTEN-SALT;
D O I
10.1080/10406638.2022.2097276
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this project, a novel magnetic nano catalyst was used in solvent-free conditions in three different experimental fabrication sections, including the synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives. Accordingly, in this study, a Carbon Quantum Dot (CQD)-based nanomagnetic catalyst (Fe3O4@CQD@Si(OEt)(CH2)(3)NH@CC@Ad@Cu(OAc)(2)) was synthesized, in which the Fe3O4 nanoparticles surface was protected using carbon quantum dots (CQDs) instead of conventional SiO2. The as-synthesized catalyst was characterized using different techniques, including Fourier transform infrared spectroscopy (FT-IR), X-ray powder Diffraction (XRD), Field Emission Scanning Electron Microscopy (FESEM), Transmission Electron Microscopy (TEM), Dynamic Light Scattering (DLS), Energy-Dispersive X-ray spectroscopy (EDX), EDX Elemental Mapping (EDX-Mapping), Thermal Gravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Vibrating Sample Magnetometer (VSM). The activity of the as-synthesized catalyst was evaluated in the synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives. The solvent-free condition with low reaction time and high reaction yield is the results of the prepared catalyst. Moreover, the effect of temperature and the amount of the catalyst (optimum reaction condition) were determined using a systematic approach, namely, the Design of Experiment (DoE). How the reaction was triggered by the catalyst was determined by FT-IR analysis.
引用
收藏
页码:5041 / 5073
页数:33
相关论文
共 85 条
[1]   A Highly Effectual and Rapid Protocol for the Synthesis of 5-Amino-1,3-diaryl-1H-pyrazole-4-carbonitriles Using 1,3-Disulfonic Acid Imidazolium Trifluoroacetate as a Dual-Functional Catalyst [J].
Abshirini, Zahra ;
Lotfifar, Nesa ;
Zare, Abdolkarim .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (05) :428-433
[2]   "2-Amino glucose" as a substrate for synthesis of magnetically recoverable nanocatalyst NiFe2O4@SiO2@amino glucose for the green synthesis of novel bis (1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)methanes [J].
Aghazadeh, Behnaz ;
Nikpassand, Mohammad .
CARBOHYDRATE RESEARCH, 2019, 483
[3]   One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation [J].
Akbarpoor, Tahere ;
Khazaei, Ardeshir ;
Seyf, Jaber Yousefi ;
Sarmasti, Negin ;
Gilan, Maryam Mahmoudiani .
RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (02) :1539-1554
[4]   Synthesis of 1-aminoalkyl-2-naphthols derivatives using an engineered copper-based nanomagnetic catalyst (Fe3O4@CQD@Si (OEt)(CH2)3NH@CC@N3@phenylacetylene@Cu) [J].
Akbarpour, Tahereh ;
Khazaei, Ardeshir ;
Yousefi Seyf, Jaber ;
Sarmasti, Negin .
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (10)
[5]   Synthesis of Pyrano [2,3-c] Pyrazole Derivatives Using a Novel Ionic-Liquid Based Nano-Magnetic Catalyst (Fe3O4@SiO2@(CH2)3NH@CC@Imidazole@SO3H+Cl-) [J].
Akbarpour, Tahereh ;
Yousefi Seyf, Jaber ;
Khazaei, Ardeshir ;
Sarmasti, Negin .
POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (06) :3843-3864
[6]   Superparamagnetic Fe3O4@Alginate supported L-arginine as a powerful hybrid inorganic-organic nanocatalyst for the one-pot synthesis of pyrazole derivatives [J].
Amirnejat, Sara ;
Nosrati, Aliakbar ;
Javanshir, Shahrzad .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (10)
[7]   Sulfamic-Acid-Functionalized Fe3-xTixO4 Nanoparticles as Novel Magnetic Catalyst for the Synthesis of Hexahydroquinolines under Solvent-Free Condition [J].
Azarifar, Davood ;
Asadpoor, Roshanak ;
Badalkhani, Omolbanin ;
Jaymand, Mehdi ;
Tavakoli, Elham ;
Bazouleh, Mona .
CHEMISTRYSELECT, 2018, 3 (48) :13722-13728
[8]   Multicomponent reaction in deep eutectic solvent for synthesis of substituted 1-aminoalkyl-2-naphthols [J].
Azizi, Najmedin ;
Edrisi, Mahtab .
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (01) :379-385
[9]  
Betti M., 1900, Gazz. Chim. Ital, V30, P310
[10]   The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].
Bur, SK ;
Padwa, A .
CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432