Catalytic application Fe3O4@SiO2 @(CH2)3-urea-dithiocarbamic acid for the synthesis of triazole-linked pyridone derivatives

被引:9
作者
Anizadeh, Mohammad Reza [1 ]
Torabi, Morteza [1 ]
Zolfigol, Mohammad Ali [1 ]
Yarie, Meysam [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan, Hamadan, Iran
基金
美国国家科学基金会;
关键词
Hydrogen bonding catalyst; Multicomponent reaction; Nanomagnetic catalyst; Pyridone; Triazole; Anomeric-based oxidation; BIOLOGICAL-BASED NANO; MAGNETIC NANOPARTICLES; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; CLICK CHEMISTRY; IONIC LIQUID; CYCLOADDITION; PYRIDINES; ANALOGS; DESIGN;
D O I
10.1016/j.molstruc.2022.134885
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this study, synthesis and characterization of an acidic-hydrogen bonding dual role and recover-able catalyst [Fe3O4 @SiO2 @(CH2)3-urea-dithiocarbamic acid] was reported. The catalyst was character-ized with several techniques such as Fourier transform-infrared spectroscopy (FT-IR), energy dispersive spectroscopy (EDS), elemental mapping (Mapp), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), thermal gravimetric analysis (TGA), derivative thermogravimetry (DTG) and vibrating sample magnetometer (VSM) analysis. Also, to review the catalytic performance of Fe3O4 @SiO2 @(CH2)3-urea-dithiocarbamic acid, we investigated the catalytic synthesis of new pyridones with 1,2,3-triazole moiety. Good yield of products, recovering and reusability of catalyst and mild reac-tion conditions can be considered as the advantages of the described catalytic system. An anomeric-based oxidation mechanism is suggested for the last step of the preparation of desired molecules.(c) 2022 Published by Elsevier B.V.
引用
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页数:10
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共 91 条
[1]   Novel magnetic propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSO3H) as a highly efficient and reusable nanoreactor for the sustainable synthesis of imidazopyrimidine derivatives [J].
Akbari, Arezoo ;
Dekamin, Mohammad G. ;
Yaghoubi, Amene ;
Naimi-Jamal, Mohammad Reza .
SCIENTIFIC REPORTS, 2020, 10 (01)
[2]   The effects of Leucaena leucocephala on semen quality, fertility and reproductive performance of dihydroxy pyridone-adapted South African Nguni goats [J].
Akingbade, AA ;
Nsahlai, IV ;
Morris, CD .
JOURNAL OF AGRICULTURAL SCIENCE, 2002, 139 :205-211
[3]   A Comprehensive Review on the Synthesis and Versatile Applications of Biologically Active Pyridone-Based Disperse Dyes [J].
Al-Etaibi, Alya M. ;
El-Apasery, Morsy Ahmed .
INTERNATIONAL JOURNAL OF ENVIRONMENTAL RESEARCH AND PUBLIC HEALTH, 2020, 17 (13) :1-13
[4]   Anomeric effect, hyperconjugation and electrostatics: lessons from complexity in a classic stereoelectronic phenomenon [J].
Alabugin, Igor, V ;
Kuhn, Leah ;
Krivoshchapov, Nikolai, V ;
Mehaffy, Patricia ;
Medvedev, Michael G. .
CHEMICAL SOCIETY REVIEWS, 2021, 50 (18) :10212-10252
[5]   Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone [J].
Alabugin, Igor, V ;
Kuhn, Leah ;
Medvedev, Michael G. ;
Krivoshchapov, Nikolai, V ;
Vil', Vera A. ;
Yaremenko, Ivan A. ;
Mehaffy, Patricia ;
Yarie, Meysam ;
Terent'ev, Alexander O. ;
Zolfigol, Mohammad Ali .
CHEMICAL SOCIETY REVIEWS, 2021, 50 (18) :10253-10345
[6]   Urea-dithiocarbamic acid functionalized magnetic nanoparticles modified with Ch-Cl: Catalytic application for the synthesis of novel hybrid pyridones via cooperative geminal-vinylogous anomeric-based oxidation [J].
Anizadeh, Mohammad Reza ;
Zolfigol, Mohammad Ali ;
Torabi, Morteza ;
Yarie, Meysam ;
Notash, Behrouz .
JOURNAL OF MOLECULAR LIQUIDS, 2022, 364
[7]   Development of a Scalable Synthesis for the Potent Kinase Inhibitor BMS-986236; 1-(5-(4-(3-Hydroxy-3-methylbutyl)-1H-1,2,3-triazol-1-yl)-4-(isopropylamino)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile [J].
Arunachalam, Pirama Nayagam ;
Kuppusamy, Prakasam ;
Ganesan, Sivakumar ;
Krishnamoorthy, Suresh ;
Nimje, Roshan Y. ;
Jarugu, Lokesh Babu ;
Chikkananjaiah, Nanjundaswamy Kanikahalli ;
Reddy, China Anki ;
Anjanappa, Prakash ;
Botlagunta, Murali ;
Vanteru, Sridhar ;
Maddala, Nageswararao ;
Shankar, Muniyappa ;
Nair, Satheesh ;
Hynes, John, Jr. ;
Santella, Joseph B., III ;
Carter, Percy H. ;
Rampulla, Richard ;
Vetrichelvan, Muthalagu ;
Gupta, Anuradha ;
Gupta, Arun Kumar ;
Mathur, Arvind .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (05) :912-918
[8]   Applications of biological urea-based catalysts in chemical processes [J].
Atashkar, Bahareh ;
Zolfigol, Mohammad Ali ;
Mallakpour, Shadpour .
MOLECULAR CATALYSIS, 2018, 452 :192-246
[9]   Novel Synthesis and Antiviral Evaluation of New Benzothiazole-Bearing N-Sulfonamide 2-Pyridone Derivatives as USP7 Enzyme Inhibitors [J].
Azzam, Rasha A. ;
Elboshi, Heba A. ;
Elgemeie, Galal H. .
ACS OMEGA, 2020, 5 (46) :30023-30036
[10]   Bifunctional Urea/Hg(OAc)2-Mediated Synthesis of 4-Aryl-6-oxycarbonyl-2-pyrones and 2-Pyridones from Dithiomalonate and β,γ-Unsaturated α-Keto Esters [J].
Bae, Daeil ;
Lee, Juyeol ;
Jin, Hui ;
Ryu, Do Hyun .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08) :6001-6014