- Boosting the catalytic performance of manganese (III)-porphyrin complex MnTSPP for facile one-pot green synthesis of 1,4-dihydropyridine derivatives under mild conditions
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In this study, the metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin manganese (III) chloride; denoted as MnTSPP) represents a promising efficient and reusable heterogeneous solid catalyst for facile and highly efficient one-pot synthesis of 1,4 dihydropyridine derivatives via three-component condensation reaction of aromatic aldehyde, ethyl acetoacetate, and ammonium acetate under green and mild reaction conditions. The simple operation, short reaction time (15 min), and the high efficiency (99%) are the special advantage of this protocol. Furthermore, the green aspects of this synthetic protocol were more studied by examination of the reusability of MnTSPP for four consecutive cycles without a significant loss of catalytic activity. Remarkably, the new synthesis presented advantages in terms of safety, commercially available catalyst, simplicity, stability, mild conditions, short reaction time, and excellent yields, using a mixture of H2O and C2H5OH environmental-friendly solvent, operationally facile, wide tolerance of starting materials, and excellent recoverable of the catalyst.
- Ali El-Remaily, Mahmoud Abd El Aleem Ali,Hamad, Hesham A.,Soliman, Ahmed M. M.,Elhady, Omar M.
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- Synthesis, characterization and cytotoxicity evaluation of a novel magnetic nanocomposite with iron oxide deposited on cellulose nanofibers with nickel (Fe3O4@NFC@ONSM-Ni)
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A heterogeneous, magnetically recoverable nanocomposite, Fe3O4@NFC@ONSM-Ni(ii) was prepared by immobilization of a novel Ni(ii) Schiff base complex on Fe3O4@NFC nanoparticles followed by treatment with melamine. This trinuclear catalyst has been characterized using several analytical techniques including FT-IR, TEM, Fe-SEM, EDX, DLS, ICP, TGA, VSM, and XRD. It was used as an efficient catalyst for one-pot solvent-free synthesis of 1,4-dihydropyridine and poly-hydro quinoline derivatives through Hantzsch reaction. This catalyst showed remarkable advantage over previously reported catalysts due to suitable conditions, short reaction time, high efficiency and lower catalyst load and timely recovery of the magnetic catalyst. Moreover, the effects of Fe3O4@NFC@ONSM-Ni(ii) nanoparticles on thein vitroproliferation of human leukemia cell line (k562) and human breast cancer cells (MDA-MB-231) were investigated. The results of MTT and Hochest assays suggested that the nanoparticles could effectively inhibit the proliferation of these cancer cells in a time- and concentration-dependent manner.
- Ghamari Kargar, Pouya,Noorian, Maryam,Chamani, Elham,Bagherzade, Ghodsieh,Kiani, Zahra
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p. 17413 - 17430
(2021/05/25)
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- Dual solvent-catalyst role of deep eutectic solvents in Hantzsch dihydropyridine synthesis
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Deep eutectic solvents are a class of new generation green solvents formed from two or more components, which furnish a new homogeneous liquid phase with lower melting point than the individual components. Here, for the first time, dual role of DES as cat
- Shaibuna,Sreekumar
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supporting information
p. 1742 - 1753
(2021/04/09)
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- Sulfonamide-functionalized covalent organic framework (COF-SO3H): an efficient heterogeneous acidic catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives
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Herein, we report the sulfonamide-functionalized covalent organic framework (COF-SO3H) prepared from melamine and terephthalaldehyde and subsequent sulfonation, as an acidic porous catalyst for the one-pot preparation of polyhydroquinoline and
- Farsi, Razieh,Mohammadi, Mohammad Kazem,Saghanezhad, Seyyed Jafar
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p. 1161 - 1179
(2020/11/18)
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- One-pot synthesis of 1,4-dihydropyridine derivatives using the Fe2ZnAl2O7 catalyzed Hantzsch three-component reaction
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A facile, low-cost, and effective one-pot method was developed for the synthesis of 1,4-dihydropyridine derivatives with high yields through the three-component reaction of ammonium acetate, ethyl acetoacetate, and aromatic aldehydes using Fe2ZnAl2O7 as catalyst. The reaction was conducted at 70–80°C temperature under solvent free conditions. The developed method had some great advantages, including safe and clean reaction conditions, high to excellent product yields, short reaction time, and a novel and powerful heterogeneous catalyst. The developed heterogeneous solid catalyst had high efficiency and reusability in one-pot multi-component syntheses such that it was easily reused four to five times without significant loss in efficiency and product yield. The catalyst was characterized by scanning Electron Microscopy (SEM)/energy-dispersive X-ray spectroscopy (EDS) and X-ray diffraction techniques. N2 sorption isotherms of the prepared nanocomposite exhibited surface area 2.1313E+01 m2/g and total pore volume of 3.0957E-02 cm3/g. Substituted dihydropyridine derivatives were characterized and confirmed using 1H NMR and 13C NMR, and elemental spectral data.
- Zargarzadeh, Reza,Akbari Dilmaghani, Karim,Nikoo, Abbas
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p. 1310 - 1316
(2021/02/16)
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- Green synthesis of benzimidazoloquinazolines and 1,4-dihydropyridines using magnetic cyanoguanidine-modified chitosan as an efficient heterogeneous nanocatalyst under various conditions
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Abstract: In the present study, we demonstrated the synthesis of magnetic cyanoguanidine-modified chitosan (MCGC) as an efficient and green retrievable heterogeneous nanocatalyst for one-pot three-component synthesis of benzimidazoloquinazolines (from 2-aminobenzimidazole, aromatic aldehydes, and dimedone) and 1,4-dihydropyridines (via Hantzsch-type condensation of ethyl acetoacetate, aromatic aldehydes, and ammonium acetate) under the ultrasonic irradiation and reflux conditions. The structure of the catalyst was fully confirmed using Fourier transform infrared spectroscopy, vibrating sample magnetometer, field emission scanning electron microscopy, energy dispersive spectroscopy, and thermogravimetric analysis. Increased amount of amino groups that are generated by modifying the surface of chitosan with cyanoguanidine as well as presence of hydroxyl groups determined the catalytic activity of MCGC. Furthermore, as experimental results confirmed, the ultrasonic-promoted reactions gave the better results in terms of reaction time, yield, and purity of isolated products. Cost effectiveness, mild conditions, low catalyst loading, convenient work-up, and ecofriendly solvent are some of the remarkable advantages of this protocol.
- Javanmiri, Kaveh,Karimian, Ramin
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p. 199 - 212
(2020/01/31)
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- Ferric Sulfasalazine Sulfa Drug Complex Supported on Cobalt Ferrite Cellulose; Evaluation of Its Activity in MCRs
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Abstract: The green and nano catalyst was simply prepared through the reaction of ferric sulfasalazine with nanomaterial CoFe2O4-cellulose as a magnetic biopolymer surface. This novel heterogeneous organometallic catalyst was charact
- Rostamizadeh, Shahnaz,Daneshfar, Zahra,Khazaei, Ali
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p. 2091 - 2114
(2020/01/31)
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- Green synthesis and characterization of novel Mn-MOFs with catalytic and antibacterial potentials
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This study focused on the synthesis of a new manganese-based metal-organic framework and the investigation of its application aspects. A Mn-MOF nanostructure, namely UoB-4, was prepared using a Schiff base organic linker (H2bbda: 4,4′-[benzene-
- Aryanejad, Sima,Bagherzade, Ghodsieh,Moudi, Maryam
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p. 1508 - 1516
(2020/02/06)
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- Efficient one-pot synthetic methods for the preparation of 3,4-dihydropyrimidinones and 1,4-dihydropyridine derivatives using BNPs?SiO2(CH2)3NHSO3H as a ligand and metal free acidic heterogeneous nano-catalyst
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Heterocyclic compounds with biological and pharmacological activates like 3,4-dihydropyrimidin-2-(1H)-ones and 1,4-dihydropyridines have attracted great interest. Boehmite nanoparticles functionalized with silylpropyl sulfamic acid (BNPs?SiO2(C
- Bahrami, Kiumars,Khodamorady, Minoo,Sohrabnezhad, Samira
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- [Fesipmim]Cl as highly efficient and reusable catalyst for solventless synthesis of dihydropyridine derivatives through Hantzsch reaction
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Abstract: In the present investigation, magnetic ferrite nanoparticles (ferrite NPs) were synthesized and coated with silica (ferrite?SiO2NPs) by using the sol-gel method. After that, silica propylmethylimidazolium chloride ionic liquid [Sipmim]Cl was prepared and linked with the above-prepared ferrite?SiO2NPs to synthesize ferrite silica propylmethylimidazolium chloride [Fesipmim]Cl catalyst. The formation of [Fesipmim]Cl catalyst was confirmed by Fourier-transform infrared (FT-IR) spectroscopy analysis. X-ray diffraction (XRD) analysis confirmed the structure of ferrite NPs and ferrite?SiO2 NPs. Transmission electron microscopy (TEM) evidenced the successful formation of ferrite NPs and ferrite?SiO2 NPs. Scanning electron microscopy (SEM) results revealed the change in morphology of ferrite NPs, ferrite?SiO2NPs and [Fesipmim]Cl. The magnetic properties of [Fesipmim]Cl catalyst were measured by vibrating sample magnetometer (VSM). The efficiency of the [Fesipmim]Cl catalyst was checked by using it for the synthesis of different derivatives of dihydropyridine through Hantzsch reaction via a three-component coupling reaction of substituted benzaldehydes, ethyl/ methyl acetoacetate and ammonium acetate. The formation and structures of all the synthesized compounds were confirmed by FT-IR, 1HNMR, 13C NMR spectral analyses. The reusability of the catalyst [Fesipmim]Cl was checked up to seven cycles and found to have excellent activity up to five cycles. Graphic abstract: [Figure not available: see fulltext.].
- Agrwal, Akansha,Kasana, Virendra
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- CoFe2O4@SiO2-NH2-CoII NPs catalyzed Hantzsch reaction as an efficient, reusable catalyst for the facile, green, one-pot synthesis of novel functionalized 1,4-dihydropyridine derivatives
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A magnetically heterogeneous CoFe2O4@SiO2-NH2-CoII nanoparticle was synthesized by the immobilization of Co (II) complex onto CoFe2O4@SiO2 nanoparticles, and the heterogeneous magnetic nanocatalyst was characterized by XRD, TEM, TGA, EDX, and FT-IR techniques. Then, the green and reusable method was introduced for a multicomponent synthesis of 1,4-dihydropyridine derivatives via Hantszch reaction. The synthesis of 1,4-dihydropyridine derivatives was proceeded by the reaction of aldehyde, ethyl acetoacetate, and ammonium acetate in the presence of this magnetic nanocatalyst in EtOH/Water (1:1). Simple work-up, short reaction times, excellent yields (60–96percent) as well as green solvent are some advantages of this novel approach, and the corresponding products were purified with no need for chromatographic separation.
- Allahresani, Ali,Mohammadpour Sangani, Mehri,Nasseri, Mohammad Ali
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- H5BW12O40-Catalyzed syntheses of 1,4-dihydropyridines and polyhydroquinolines via Hantzsch reaction: Joint experimental and computational studies
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A series of polyhydroquinoline derivatives were effectively synthesized via Hantzsch reaction in high yields in the presence of catalytic amounts of a highly negatively charged borotungstic acid H5BW12O40 in refluxing EtOH under green and mild reaction co
- Momeni, Tayebeh,Heravi, Majid M.,Hosseinnejad, Tayebeh,Mirzaei, Masoud,Zadsirjan, Vahideh
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- Trinuclear cis-dioxidomolybdenum(VI) complexes of compartmental C3 symmetric ligands: Synthesis, characterization, DFT study and catalytic application for hydropyridines (Hps) via the Hantzsch reaction
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Trinuclear cis-dioxidomolybdenum(VI) complexes of the type [{MoVIO2(MeOH)}3L1-7] (1–7) have been synthesized using tris(H2ONO) donor ligands [H6L1-7 (I–VII)] assembled from benzene-1,3,5-tricarbohydrazide (bthz) and the corresponding salicylaldehyde (sal). All the ligands and the complexes were characterized by numerous techniques, such as FT-IR, UV–visible, NMR (1H and 13C) spectroscopy, electrochemical study, elemental analysis, thermogravimetric study and single crystal X-ray diffraction of the ligand III and complexes 1 and 5. In the presence of H2O2 as an oxidant, these complexes show excellent catalytic potential towards the one-pot three-components [ethyl acetoacetate, benzaldehyde (or its derivatives) and ammonium acetate] dynamic covalent assembly in the Hantzsch reaction. Under solvent free conditions, as high as 98% conversion along with 100% selectivity towards diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (1,4-DHP) has been achieved in 1 h. Although solvents do not improve the conversion, they do influence the selectivity of the products. With the elapse of time, the conversion of dihydropyridine to the diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate derivative occurs and completes in ca. 10 h with a distinct color change, showing the importance of the catalysts. Efforts have been made to provide suitable reaction pathways for the catalytic reaction based on spectroscopic and density functional theory studies.
- Avecilla, Fernando,Gupta, Puneet,Maurya, Mannar R.,Tomar, Reshu
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supporting information
(2020/06/08)
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- MIL-101-SO3H metal-organic framework as a Br?nsted acid catalyst in Hantzsch reaction: An efficient and sustainable methodology for one-pot synthesis of 1,4-dihydropyridine
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A straightforward and efficient methodology for the one-pot multicomponent synthesis of 1,4-dihydropyridine has been developed using MIL-101-SO3H metal-organic framework as a solid Br?nsted acid. The presence of the uniformly distributed Br?nsted acidic sulfonic acid sites throughout the framework and the high stability bestow the catalyst with excellent reactivity towards the synthesis of 1,4-dihydropyridine under simple reaction conditions using renewable ethanol as the solvent. The present methodology tolerates various functional groups and allows the synthesis of 1,4-dihydropyridine derivatives in good to excellent yields through Hantzsch reaction. The developed methodology proceeds under mild conditions, avoids corrosive reagents and special reaction conditions, and is amenable to gram scale synthesis. The sustainable nature of the catalyst was proved by the easy recovery and the reusability of the catalyst, as it was reused several times without loss in activity, which was confirmed from the FTIR, PXRD and SEM analyses of the reused catalyst.
- Devarajan, Nainamalai,Suresh, Palaniswamy
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p. 6806 - 6814
(2019/05/10)
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- Anchored sulfonic acid on silica-layered NiFe2O4: A magnetically reusable nanocatalyst for Hantzsch synthesis of 1,4-dihydropyridines
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In this study, the immobilization of sulfonic acid on silica-layered nickel ferrite, NiFe2O4@SiO2@SO3H, was investigated. The sulfonated Ni-nanocatalyst was then characterized using FT-IR, SEM, EDX, XRD and VSM analyses. Catalytic activity of the Ni-nanocomposite was also studied towards Hantzsch synthesis of 1,4-dihydropyridines via one-pot condensation reaction of 1,3-diketones (ethyl acetoacetate or 4-hydroxycoumarin), aromatic aldehydes and aqueous ammonia in H2O (70 °C)as a green solvent. All reactions were carried out within 10–100 min to afford the products in high to excellent yields. The green aspect of this synthetic protocol was more studied by examining the reusability of NiFe2O4@SiO2@SO3H MNPs for seven consecutive cycles without the significant loss of catalytic activity. The current method represents remarkable advantages in terms of mild reaction conditions, using H2O as an environmental-friendly solvent, stability and easy separation of the magnetic nanocatalyst, high yield of products, wide tolerance of starting materials and the perfect reusability of the applied Ni-nanocatalyst.
- Zeynizadeh, Behzad,Rahmani, Soleiman,Eghbali, Elham
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- Preparation method and application of novel ionic beta-naphthol aldehyde Schiff base zirconium complex
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The invention belongs to the technical field of catalytic organic synthesis, and particularly relates to a preparation method and application of a novel ionic beta-naphthol aldehyde Schiff base zirconium complex. Zirconium atoms are coordinated with a beta-naphthol aldehyde Schiff base ligand and water molecules, and two perfluoroalkyl (aryl) sulfonic acid groups are combined with central atom zirconium through covalent bonds and ionic bonds respectively. The preparation method comprises the following steps: dissolving beta-naphthol aldehyde Schiff base zirconium dichloride in a solvent, adding a silver salt under the protection of N2, reacting the mixture for 1-4 hours in a dark place at room temperature, performing filtration, adding n-hexane into filtrate until layering, putting the solution into a refrigerator, and freezing the solution for 24 hours to separate out the beta-naphthol aldehyde Schiff base zirconium complex. The beta-naphthol aldehyde Schiff base zirconium complex hashigh air stability and strong Lewis acidity, and can efficiently catalyze the Hantzsch reaction of aldehyde, beta-ketoester and ammonium acetate to synthesize 1,4-dihydropyridine derivatives.
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Paragraph 0041; 0044-0045
(2019/12/02)
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- The First Recyclable, Nanocrystalline CdS Thin Film Mediated Eco-benign Synthesis Of Hantzsch 1, 4 Dihyropyridines, 1, 8-Dioxodecahydroacridine and Polyhydroquinolines derivatives
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In the present study, we report a recyclable, nanocrystalline CdS thin film mediated efficient one-pot, three component synthesis of Hantzsch 1, 4 Dihydropyridine in good yields. The catalyst is also effective for the efficient synthesis of Polyhydroquinoline and 1, 8-dioxodecahydroacridine derivatives in good to excellent yields. The CdS thin film catalyst was prepared by chemical bath deposition (CBD) technique. The cadmium sulphide thin film was characterized by powder XRD and FT-IR studies. The average crystallite size (D) was calculated from powder XRD by using Scherrer formula and SEM analysis. The elemental composition of the CdS thin film was established by EDS analysis. The effect of temperature, substituent's, catalyst loading and mole ratio on the reaction was also studied. All the products were thoroughly characterized by 1H-NMR, 13C-NMR, FT-IR, Mass spectral and CHN analysis. A plausible mechanism for the CdS thin film catalyzed synthesis of 1, 4 DHP's is proposed. The heterogeneous catalyst could be easily recovered from the reaction mixture and successively reused at least five times without loss of activity.
- Lavanya,Venkatapathy,Magesh,Perumal,Sathishkumar,Amudha
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- A novel method for synthesis of 1,4-dihydropyridines using robust laterite catalyst under ultrasonic irradiation
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An efficient method for the synthesis of 1,4-dihydropyridine derivatives from various aryl or heteroaryl aldehydes, β-ketoester and ammonium acetate in presence of laterite catalyst in ethanol under ultrasonication is reported. Catalyst study done with wet chemical analysis, FT-IR, XRD, SEM and EDS techniques. The catalyst can be recovered and reused without noticeable loss of activity even after five cycles.
- Chine,Patil
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p. 128 - 134
(2018/12/11)
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- Cellulose matrix embedded copper decorated magnetic bionanocomposite as a green catalyst in the synthesis of dihydropyridines and polyhydroquinolines
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A new biopolymer-based magnetic nanocomposite was prepared and characterized by Fourier transform infrared (FT-IR) spectroscopy, energy-dispersive X-ray (EDX) analysis, scanning electron microscopy (SEM) and transmission electron microscopy (TEM) images,
- Maleki, Ali,Eskandarpour, Vahid,Rahimi, Jamal,Hamidi, Negar
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p. 251 - 260
(2019/01/03)
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- Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives
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A convenient strategy for synthesis of the various derivatives of 1,4-dihydropyridine (1,4-DHP), as one of the most important pharmaceutical compounds, is presented in this study. For this purpose, firstly, magnetic iron oxide nanoparticles (Fe3O4 NPs) were fabricated and suitably coated by silica network (SiO2) and trimethoxy vinylsilane (TMVS). Then, their surfaces were well functionalized with pyrimidine-2,4-diamine (PDA) as the main active sites for catalyzing the synthesis reactions. In this regard, the performance of three different methods including reflux, microwave (MW) and ultrasound wave (USW) irradiations have been comparatively monitored via studying various analyses on the fabricated nanocatalyst (Fe3O4/SiO2-PDA). Concisely, high efficiency of the USW irradiation (in an ultrasound cleaning bath with a frequency of 50 kHz and power of 250 W/L) has been well proven through the investigation of the main factors such as excellent surface-functionalization, core/shell structure conservation, particle uniformity, close size distribution of the particles, and great inhibition of the particle aggregation. Then, the effectiveness of the USW irradiation as a promising co-catalyst agent has been clearly demonstrated in the 1,4-DHP synthesis reactions. It has been concluded that the USW could provide more appropriate conditions for activation of the catalytic sites of Fe3O4/SiO2-PDA NPs. However, high reaction yields (89%) have been obtained in the short reaction times (10 min) due to the substantial synergistic effect between the presented nanocatalyst and USW.
- Taheri-Ledari, Reza,Rahimi, Jamal,Maleki, Ali
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- Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds
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An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.
- Ghosh, Santanu,Jana, Chandan K.
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supporting information
p. 10153 - 10157
(2019/12/26)
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- Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate derivative for inducing cell apoptosis, a method for producing the same, and an anticancer drug containing the same
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The present invention relates to a diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate derivative which induces cell apoptosis, a method of manufacturing the same, and an anti-cancer drug containing the same. A compound represented by chemical form
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Paragraph 0133-0136; 0158-0159; 0170-0171
(2019/04/05)
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- Poly(vinylimidazolum acetic acid)-entrapped nanozeolite: efficient heterogeneous catalyst for synthesis of polyhydroquinolines and 1,4-dihydropyridines
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An effective method for synthesis of substituted 1,4-dihydropyridines and polyhydroquinoline derivatives by Hantzsch reaction using poly(ionic liquid)-based nanozeolite (NZ@PIL-COOH) catalyst under simple conditions is described. The new solid acid catalyst was prepared by polymerization of 3-carboxymethyl-1-vinylimidazolium in presence of modified nanozeolite, and characterized by Fourier-transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD) analysis, and transmission electron microscopy (TEM). The resulting heterogeneous catalyst displayed high catalytic performance under mild reaction condition in short reaction time. The catalyst was recycled eight times without any loss in reactivity or yield.
- Amoli, Tabassom,Baghbanian, Seyed Meysam
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p. 3389 - 3405
(2018/02/22)
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- Preparation and characterization of doped Sr.2Co.8Fe12O19 hexaferrite: An efficient heterogeneous catalyst for one pot synthesis of 1,4-dyhydropyridine derivatives
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A clean and efficient method has been developed for the synthesis of 1,4-dihydropyridine derivatives using aromatic aldehyde, ethyl acetoacetate, and ammonium acetate using cobalt doped strontium hexaferrite under microwave irradiation conditions. This pr
- Aswar,Ladole
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p. 1525 - 1530
(2020/06/27)
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- Synthesis and application of chitosan supported vanadium oxo in the synthesis of 1,4-dihydropyridines and 2,4,6-triarylpyridines: Via anomeric based oxidation
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Chitosan, as a biopolymer, exhibits a strong affinity for complexation with suitable metal ions. Thus, it has received increased attention for the preparation of stable bioorganic-inorganic hybrid heterogeneous catalysts. Herein, a novel chitosan based vanadium oxo (ChVO) catalyst was prepared and fully characterized by several techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), derivative thermal gravimetric (DTG), differential thermal analysis (DTA), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), high-resolution transmission electron microscopy (HRTEM), selected area electron diffraction (SAED), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma mass spectrometry (ICP-MS). The synthesized catalyst has been successfully used as a reusable catalyst in the synthesis of dihydropyridines and triarylpyridines.
- Safaiee, Maliheh,Ebrahimghasri, Bahar,Zolfigol, Mohammad Ali,Baghery, Saeed,Khoshnood, Abbas,Alonso, Diego A.
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p. 12539 - 12548
(2018/08/04)
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- A novel three-phenyl bismuth organic (V) complex catalyst and its preparation method and a nitrogen-containing compound in the synthesis of the catalytic application
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The invention provides a novel triphenyl organic bismuth (V) complex catalyst I, a preparation method thereof, and a synthesis method for nitrogen-containing compounds II-V under the catalysis of the novel triphenyl organic bismuth (V) complex catalyst I. The complex I is a cation-type organic bismuth complex, and the molecular formula is Ph3BiX2 (X=OSO2C4F9, OSO2C6F5, OSO2C8F17). The bismuth atom in the complex is connected with three triphenyls to show pentavalence. The other two perfluorooctane sulfonate roots and the cation part of the complex form an ionic bond. The synthesis method is used for synthesizing four types nitrogen-containing compounds, including bis(indolyl)methane II, dihydropyrimidinone III, dihydropyridine IV and beta-alkamine V, by taking the triphenyl organic bismuth compound as a catalyst and a conventional organic solvent as a reaction solvent. The method has the advantages of lower cost, high yield, simplicity and convenience in operation, zero pollution, repeated use of the catalyst and the like, and creates a cheap and environment-friendly way for preparing the nitrogen-containing compounds.
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Paragraph 0173; 0174
(2018/10/19)
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- Facile template-free route to fabricate core–shell Fe3O4@PANI-SO3H urchin-like nanoparticles as reusable catalyst for Hantzsch reaction: change morphology upon sulfonation
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Abstract: This paper describes a novel and effective approach to fabricate the core–shell Fe3O4@PANI-SO3H urchin-like morphology in a self-assembly method as nano-magnetic solid acid catalyst. The Fe3O4@PANI microspheres were synthesized via an in situ surface polymerization of aniline monomer in an acidic condition, using ammonium persulfate as the oxidant. It was found that upon sulfonation of polyaniline (PANI), the morphology changes to morphology similar to urchin confirming the transmission electron microscopy and field emission scanning electron microscopy results. The as-prepared solid acid catalyst was also carefully analyzed by energy-dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis and vibrating sample magnetometry. This new magnetic core–shell material was shown to have high catalytic performance for one–pot synthesis of 1,4-dihydropyridine derivatives. In addition, the catalyst can be easily separated using an external magnet. Recyclability and reusability for several runs, facile accessibility, and simple handling are the merits of this magnetic-heterogeneous acid catalyst. Graphical Abstract: [Figure not available: see fulltext.].
- Shahamat, Zahra,Nemati, Firouzeh,Elhampour, Ali
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p. 6649 - 6666
(2018/06/25)
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- The efficient synthesis of Hantzsch 1,4-dihydropyridines via metal-free oxidative C–C coupling by HBr and DMSO
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A novel and efficient synthesis of Hantzsch 1,4-dihydropyridines through metal-free oxidative C–C coupling process was described. The reaction between benzylic alcohols, 1,3-dicarbonyl compounds and ammonium hydroxide in the presence of HBr in DMSO at 75 °C led to afford 1,4-dihydropyridine in excellent yields. This protocol introduces the use of benzyl alcohols instead of aldehydes as a new modification of the Hantzsch reaction.
- Rezaei, Narjes,Ranjbar, Parviz Rashidi
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p. 4102 - 4106
(2018/10/20)
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- Highly effective Br?nsted base/lewis acid cooperative catalysis: A new Cd metal-organic framework for the synthesis of Hantzsch 1,4-DHPs at ambient temperature
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A new 3D metal-organic framework {[Cd3(BDC)3(OPP)(DMF)2]·2DMA}n (TMU-33) has been synthesized using a novel V-shaped imine-functionalized ligand, N,N′-(oxybis(4,1-phenylene))bis(1-(pyridin-4-yl)methanimine) (OPP), terephthalic acid (H2BDC), and Cd(NO3)2·4H2O and has been fully characterized. The function of the imine moiety of the OPP ligand as a Br?nsted base and open Cd site as a Lewis acid in this framework was investigated to determine the role of the cooperative catalyst in the synthesis of Hantzsch 1,4-dihydropyridines simultaneously and separately at ambient temperature. In addition, nanorods and nanoplates of TMU-33 were synthesized via a sonochemical reaction by the coordination modulation method, and the effect of the nanostructure on the relative accessibility of the catalytic site was studied. Moreover, the catalytic performance of TMU-33 with different morphologies was evaluated in this reaction. Efficient catalytic activity was observed for the nanoscale catalysts at ambient temperature, and the acidic sites in the cooperative catalyst were found to be more effective than the existing basic sites in the structure. TMU-33 can be reused by washing with ethanol at least four times with no significant degradation of the catalytic activity (less than 7%).
- Rouhani, Farzaneh,Morsali, Ali
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p. 15475 - 15484
(2017/12/15)
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- Method for synthesizing 1,4-dihydropyridines derivatives
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The invention relates to a method for synthesizing 1,4-dihydropyridines derivatives. According to the method, a fluorescence-marked nonmetal organic boron-nitrogen lewis acid-alkali dual-functional complex is used as a catalyst, so that the pollution of heavy metals is effectively avoided; the catalyst can be recycled, and a residual amount of the catalyst in a product can be rapidly detected; and the source of raw materials is wide, the target yield is close to 100 percent, the reaction process is a homogenous reaction, and a product is obtained by virtue of chromatographic separation. The whole reaction system can be directly amplified, and the industrialization prospect is significant.
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Paragraph 0116; 0117
(2017/10/27)
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- A New Type of Magnetically-Recoverable Heteropolyacid Nanocatalyst Supported on Zirconia-Encapsulated Fe3O4 Nanoparticles as a Stable and Strong Solid Acid for Multicomponent Reactions
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Abstract: A novel highly efficient magnetically retrievable catalyst was developed by the immobilization of H3PW12O40 (20–60 wt%) on the surface of zirconia-encapsulated Fe3O4 nanoparticles. The prepared HPW supported on nano-Fe3O4@ZrO2 heterogeneous acid catalyst (or n-Fe3O4@ZrO2/HPW) was fully characterized by several physicochemical techniques such as: Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The FT-IR spectroscopic data revealed that H3PW12O40 molecules on the nano-Fe3O4@ZrO2 support existed in the Keggin structure. The acidity of the catalyst was measured by the help of a potentiometric titration with n-butylamine. It was surprising that this very strong solid acid catalyst exhibited an excellent acid strength which was as a result of possessing a higher number of surface active sites compared to its homogeneous analogues. The catalytic activity of the as-prepared novel nano-Fe3O4@ZrO2/HPW was explored through the one-pot three-component synthesis of different 3,4-dihydropyrimidin-2(1H)-ones (i.e. Biginelli reaction) and 1,4-dihydropyridines (i.e. Hantzsh reaction) under solvent free condition. The sample of 40 wt% showed higher acidity and activity in the catalytic transformation. After the reaction, the catalyst/product isolation could be easily achieved with an external magnetic field and the catalyst could be easily recycled for at least five times without any decrease in its high catalytic activity. The excellent recyclability was attributed to the strong interaction between the hydroxyl groups of the nano-Fe3O4@ZrO2 support and the HPW species. Graphical Abstract: [Figure not available: see fulltext.].
- Zolfagharinia, Somayeh,Kolvari, Eskandar,Koukabi, Nadiya
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p. 1551 - 1566
(2017/05/17)
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- Fe3O4@SiO2 supported aza-crown ether complex cation ionic liquids: preparation and applications in organic reactions
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A series of aza-crown ether ionic liquids supported on magnetic Fe3O4@SiO2 core-shell particles were designed, synthesized and characterized by elemental analysis, TEM, TG and FT-IR. These new aza-crown ether complex cation ionic liquids were utilized as heterogeneous acidic catalysts in Friedel-Crafts alkylation and Hantzsch reaction in good yields under convenient reaction conditions. Moreover, these magnetic particle supported IL catalysts could be readily recovered by an external magnet and reused five times without obvious loss of activity.
- Li, Dandan,Wang, Jinyuan,Chen, Fengjuan,Jing, Huanwang
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p. 4237 - 4242
(2017/02/05)
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- Sulfated polyborate: An efficient and reusable catalyst for one pot synthesis of Hantzsch 1,4-dihydropyridines derivatives using ammonium carbonate under solvent free conditions
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A simple and efficient method for the synthesis of four-component 1,4-dihydropyridines of various aldehydes, β-ketoesters and ammonium carbonate catalyzed by sulfated polyborate with high yields under a solvent free condition at 90?°C is described. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
- Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
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supporting information
p. 1240 - 1244
(2017/03/02)
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- Hollow Fe3O4@DA-SO3H: an efficient and reusable heterogeneous nano-magnetic acid catalyst for synthesis of dihydropyridine and dioxodecahydroacridine derivatives
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Abstract: In this work, for the first time, a highly stable and efficient super-paramagnetic catalyst, H-Fe3O4@DA-SO3H, involving hollow morphology of Fe3O4 as core and dopamine as shell was prepared
- Mirhosseyni, Marzie sadat,Nemati, Firouzeh,Elhampour, Ali
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p. 791 - 801
(2017/02/26)
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- Synthesis and in vitro evaluation of Ca2 + channel blockers 1,4-dihydropyridines analogues against Trypanosoma cruzi and Leishmania amazonensis: SAR analysis
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Drugs containing the1,4-dihydropyridine (DHP) core have recently attracted attention concerning their antiparasitic effect against various species of Leishmania and Trypanosoma. This approach named drugs repositioning led to interesting results, which have prompted us to prepare 21 DHP's analogues. The 1,4-DHP scaffold was decorated with different function groups at tree points including the nitrogen atom (NH and N-phenyl), the aryl group attached to C-4 (various substituted aryl residues) and the carbon atoms 2 and 6 (bearing Ph or Me groups). Moreover, the products were evaluated for their cytotoxicity on three cancer and a non-tumoral cell lines. Only 6 of them were antiproliferative and their weak effect (CC50 comprised between 27 and 98 μM) suggested these DHPs as good candidates against the intracellular amastigote forms of L. amazonensis and T. cruzi. L. amazonensis was sensitive to DHPs 5, 11 and 15 (IC50 values at 15.11, 45.70 and 53.13 μM, respectively) while 12 of them displayed significant to moderate trypanocidal activities against T. cruzi. The best trypanocidal activities were obtained with compounds 2, 18 and 21 showing IC50 values at 4.95, 5.44, and 6.64 μM, respectively. A part of the N-phenylated DHPs showed a better selectivity than their NH analogues towards THP-1 cells. 4-Chlorophenyl, 4-nitrophenyl and 3-nitrophenyl residues attached to the carbon atom 4 turned to be important sub-structures for the antitrypanosomal activity.
- Pollo, Luiz A.E.,de Moraes, Milene H.,Cisilotto, Júlia,Creczynski-Pasa, Tania B.,Biavatti, Maique W.,Steindel, Mario,Sandjo, Louis P.
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p. 789 - 797
(2017/09/23)
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- Computational investigations on structural and electronic properties of CuI nanoparticles immobilized on modified poly(styrene-co-maleic anhydride), leading to an unexpected but efficient catalyzed synthesis of 1,4-dihydropyridine via Hantzsch pyridine synthesis
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A, quantitative description for the interaction of Cu(I) with poly(styrene-co-maleic anhydride) modified with 4-aminopyridine (denoted as CuI/SMI complex) is presented using density functional theory (DFT) and quantum theory of atoms in molecules (QTAIM) approaches. Topological analysis of electron density revealed the existence of effective interactions between Cu(I) ions and the nitrogen in the pyridine ring. Interestingly, the results also showed that there is considerable interaction between Cu(I) and the oxygen of the carbonyl motif in the SMI ligand. Thus, CuI/SMI was examined as a heterogeneous and recyclable catalyst in Hantzsch pyridine synthesis under solvent-free conditions, affording diverse 1,4-dihydropyridines (1,4-DHPs) in excellent yields with relatively short reaction times.
- Heravi, Majid M.,Hosseinnejad, Tayebeh,Nazari, Niousha
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p. 530 - 536
(2017/05/31)
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- Cu–S-(propyl)-2-aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides
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Cu–S-(propyl)-2-aminobenzothioate supported on functionalized Fe3O4 magnetic nanoparticles is reported as a reusable and highly efficient nanocatalyst for the one-pot synthesis of polyhydroquinoline derivatives and also for selective
- Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Moradi, Parisa,Havasi, Nasrin
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p. 619 - 625
(2016/07/19)
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- Tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst for one-pot synthesis of Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives
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Abstract: A green, convenient, and environment-friendly approach for the synthesis of biologically active Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives in the presence of tetraethylammonium 2-(carbamoyl)benzoate, as an effective bifunctional metal-free catalyst, has been developed via a one-pot multicomponent reaction of various aldehydes, ethyl acetoacetate or cyclic 1,3-dicarbonyl compounds, and ammonium acetate in EtOH under reflux conditions. The proposed methodology is capable of providing the desired products in good to excellent yields and short reaction time with straightforward work-up and a low-cost procedure. Graphical abstract: [Figure not available: see fulltext.]
- Yarhosseini, Mahsa,Javanshir, Shahrzad,Dekamin, Mohammad G.,Farhadnia, Mohammad
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p. 1779 - 1787
(2016/09/28)
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- A Simple and Efficient One-pot Synthesis of 1,4-dihydropyridines Using Nano-WO3-supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent-free Conditions
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Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.
- Bitaraf, Mehrnoosh,Amoozadeh, Ali,Otokesh, Somayeh
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p. 336 - 344
(2016/05/09)
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- An efficient solvent-free synthesis of isoxazolyl-1,4-dihydropyridines on solid support SiO2 under microwave irradiation
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An efficient synthesis of 1,4-dihydropyridines was developed. 1,4-Dihydropyridines were synthesized starting from various 3-substituted isoxazolyl-5-carbaldehydes, ethyl acetoacetate, and ammonium acetate under microwave irradiation and solvent-free conditions (86–96?%), and were characterized by HRMS, FT-IR, 1H NMR, and 13C NMR spectroscopy. Solid support SiO2 was found to possess favorable catalysis and dispersancy for the condensation reaction. The merits of the method included the environmental friendly reaction conditions, simple operation, extensive substrates, good yields and reuse of the SiO2. Moreover, the crystal structure of compound diethyl 4-[3-(2-methoxyphenyl)isoxazol-5-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in orthorhombic Pbca space group was presented. Graphical abstract: [Figure not available: see fulltext.]
- Zhang, Dawei,Chen, Xiaodong,Guo, Xue,Zhang, Yumin,Hou, Yaya,Zhao, Tianqi,Gu, Qiang
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p. 1605 - 1614
(2016/08/16)
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- Synthesis of hantzsch 1,4-dihydropyridines in a continuous flow microreactor
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A simple and efficient synthesis of Hantzsch 1,4-dihydropyridines from the condensation of benzaldehydes with alkyl acetoacetates/benzoylacetate and aqueous ammonia in the absence of catalyst has been developed by using a continuous flow microreactor. Under optimized condition, various 1,4-dihydropyridines were obtained in 80-93% yield with high atom efficiency. Compared with using batch system, the present smooth procedure greatly accelerated the reaction due to the excellent mixing and mass transfer of reactant in micro flow system.
- Gao, Peiyuan,Sun, Xuan,Lei, Ming,Zhang, Hong
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p. 755 - 761
(2017/04/10)
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- Potential applications of Zr-KIT-5: Hantzsch reaction, Meerwein-Ponndorf-Verley (MPV) reduction of 4-tert-butylcyclohexanone, and Prins reaction of citronellal
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The acidity of Zr-incorporated large pore cubic mesoporous silicate, KIT-5, with Fm3m symmetry was explored as catalyst in the Hantzsch reaction for preparation of 1,4-dihydropyridine (DHP) derivatives, Meerwein-Ponndorf-Verley (MPV) reduction of 4-tert-b
- Srinivasan, Vinju Vasudevan,Ranoux, Adeline,Maheswari, Rajamanickam,Hanefeld, Ulf,Ramanathan, Anand,Subramaniam, Bala
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p. 2399 - 2408
(2016/03/16)
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- Air-stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N-Containing Compounds
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Triphenyl bismuth bisperfluorooctanesulfonate is an air- and water-stable Lewis acid. It exhibits high catalytic efficiency for the synthesis of nitrogen heterocycles such as diindolylmethane derivatives, dihydropyrimidinones, dihydropyridines and 1,2-disubstitued benzimidazoles under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles.This catalytic system affords a simple and efficient way for the synthesis of N-containing compounds.
- Wang, Penghui,Wang, Jinying,Au, Chak-Tong,Qiu, Renhua,Xu, Xinhua,Yin, Shuang-Feng
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supporting information
p. 1302 - 1308
(2016/04/26)
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- Synthesis and Cytotoxicity of 1,4-Dihydropyridines and an Unexpected 1,3-Oxazin-6-one
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Eight heterocycles have been prepared in a one-pot reaction manner based on the Hantzsch dihydropyridine synthesis. The synthesis afforded seven dihydropyridines (DHP) and one unexpected 1,3-oxazin-6-one. Their structures were confirmed based on NMR spect
- Sandjo, Louis Pergaud,Kuete, Victor,Nana, Frederic,Kirsch, Gilbert,Efferth, Thomas
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p. 310 - 314
(2016/05/19)
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- Synthesis and characterization of Ni(II)-Vanillin-Schiff base-MCM-41 composite as an efficient and reusable nanocatalyst for multicomponent reactions
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An efficient heterogeneous catalyst (Ni(ii)-Vanillin-Schiff base-MCM-41) has been synthesized by immobilization of nickel(ii)-vanillin complex on MCM-41 nanostructure and characterized by XRD, TGA, BET, EDS, SEM, ICP-OES, TEM and FT-IR spectroscopy. The catalytic activity and stability of the prepared compound has been studied in some multicomponent reactions with polyhydroquinoline, 1H-indazolo[1,2-b]phthalazine-trione and 2,3-dihydroquinazolin-4(1H)-one derivatives under mild condition reactions. All the reactions were carried out in the presence of water as the solvent and under solvent-free conditions. The simple work up, mild conditions, excellent yield, inexpensive and non-toxic catalyst; makes this protocol both attractive and economically viable. More importantly, this catalyst can be reused several times without any significant loss of its catalytic activity.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Khanmoradi, Maryam
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p. 56549 - 56561
(2016/07/06)
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- Cu-doped ZnO nanocrystalline powder as a catalyst for green and convenient multi-component synthesis of 1,4-dihydropyridine
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Abstract A simple, efficient, and convenient one-step method for synthesis of Hantzsch 1,4-dihydropyridine, using Cu-doped ZnO nanocrystalline powder as a catalyst is reported. The method offers several advantages including excellent yields, green solvent, easy work-up, simplicity in operation and catalyst reusability.
- Alinezhad, Heshmatollah,Mohseni Tavakkoli, Sahar
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p. 5931 - 5940
(2015/08/18)
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- SnCl4-functionalized nano-Fe3O4 encapsulated-silica particles as a novel heterogeneous solid acid for the synthesis of 1,4-dihydropyridine derivatives
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A novel type of green heterogeneous solid acid was prepared by the immobilization of SnCl4 on the surface of Fe3O4@SiO2 (Fe3O4@SiO2-SnCl4) and characterized by Fourier
- Bamoniri, Abdolhamid,Fouladgar, Sara
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p. 78483 - 78490
(2015/10/05)
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- N-Propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride-SBA-15 (SBA-DABCO) as basic mesoporous catalyst for the synthesis of 1,4-dihydropyridine hetrocyclic compounds
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Regarding the green chemistry's goals, the development of mesoporous silica materials as attractive candidates in the search for supporting of catalysts is currently a subject of increasing interest. Therefore, in the present research n-propyl-4-aza-1-azo
- Kiasat, Ali Reza,Davarpanah, Jamal
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p. 179 - 182
(2015/07/07)
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- Melamine supported on hydroxyapatite-encapsulated-γ-Fe2O3: A novel superparamagnetic recyclable basic nanocatalyst for the synthesis of 1,4-dihydropyridines and polyhydroquinolines
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In this paper, the preparation and characterization of hydroxyapatite-encapsulated γ-Fe2O3 nanoparticles functionalized with Melamine nanocomposite (γ-Fe2O3@HAp@Melamine) are presented. The resulting nanocomposite was characterized by infrared spectroscopy, scanning electron microscope, thermal gravimetric analysis, X-ray diffraction, vibrating sample magnetometer and elemental analysis. The catalytic activity of γ-Fe2O3@ HAp@Melamine as a magnetic powerful basic nanocatalyst was probed through one-pot synthesis of 1, 4-dihydropyridine and polyhydroquinoline derivatives through Hantzsch condensation reaction under solvent-free thermal conditions. The heterogeneous catalyst could be recovered easily by simple magnetic decantation and reused many times without significant loss of its catalytic activity.
- Igder, Sedighe,Kiasat, Ali Reza,Shushizadeh, Mohamad Reza
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p. 7227 - 7244
(2015/09/29)
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- Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions
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Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.
- Palakshi Reddy,Sarveswari,Vijayakumar
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p. 6877 - 6883
(2015/08/18)
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