MgAl2O4 spinel-type as highly efficient catalyst for one-pot synthesis of 4H-pyrans

2022 ◽  
Vol 16 ◽  
Author(s):  
Mustapha Dib ◽  
Marieme Kacem ◽  
Soumaya Talbi ◽  
Hajiba Ouchetto ◽  
Khadija Ouchetto ◽  
...  

Background: Pyran is an heterocyclic oxygen-containing compound that displays a wide range of therapeutic activities. Additionally, pyran is also one of the important structural subunits widely found in pharmaceuticals products. This makes it a recent focus for researchers from the industry and academic institutions. Herein, we reported an efficient and environmentally friendly one-pot strategy for the synthesis of bioactive 4H-pyran compounds via a multicomponent reaction of ethyl acetoacetate, malononitrile and substituted aromatic aldehydes in the presence of the heterogeneous spinel catalyst ( MgAl2O4 ) under mild conditions (room temperature and green solvents). The MgAl2O4 nanocatalyst was prepared from Mg/Al-LDH with a molar ratio 3 of Mg2+/Al3+ by heat treatment at 800°C. The samples were studied by a various characterization techniques such as XRD, TG-dTG, FT-IR and N2 adsorption-desorption. Good to excellent yields and facile separation of the catalyst from the reaction mixture are two of the most appealing features of this approach. Thus, bioactive molecules with pyran units may have fascinating biological properties. An efficient and green strategy for the one-pot synthesis of bioactive 4H-pyran compounds has been described. The pyrans heterocycles were produced by multicomponent reaction of ethyl acetoacetate, malononirile and substituted aromatic aldehydes in the presence of MgAl2O4 spinel nanocatalyst under mild conditions (room temperature and green solvents). MgAl2O4 nanocatalytst was prepared from Mg/Al-LDH with a molar ratio 3 of Mg2+/Al3+ by thermal treatment at 800°C. The samples were investigated by various characterization techniques such as XRD, TG-dTG, FT-IR and N2 adsorption-desorption. The following are the appealing qualities of this unique strategy including good to exceptional yields, and ease of separation of catalyst from the reaction mixture. Thus, the obtained bioactive compounds containing pyrans motif can be exhibiting interested biological activities. Methods: The substituted 4H-pyran compounds were carried out by condensation reaction of substituted aromatic aldehydes, ethyl ethyl acetoacetate and malononirile by using MgAl2O4 nanocatalyst under sustainable conditions. Objective: To develop an efficient methodology for synthesis of 4H-pyran heterocyclic molecules may have interesting applications in biology using a heterogeneous and easily synthesized catalyst. Results: This procedure outlines the synthesis of bioactive compounds in good yields and with ease of catalyst extraction from the reaction mixture under sustainable reaction conditions. Conclusion: In conclusion, it is important to reiterate that a spinel nanostucture has been successfully prepared and fully characterized using different physicochemical analysis methods. The catalytic activity of this heterogeneous catalyst was examined through the one-pot condensation of aryl benzaldehyde, malononitrile and ethyl acetoacetate. Therefore, we have developed a green method for the preparation of 4H-pyrans derivatives using MgAl2O4 as an efficient heterogeneous catalyst. The reactions were performed under green conditions, which have many benefits such as undergoing a simple procedure, good to excellent yields and easy to separate the catalyst.

SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.


1991 ◽  
Vol 46 (8) ◽  
pp. 978-984 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Thomas Großpietsch

The reaction of perfluoro-2-phosphapropene F3CP=CF2 (1) with tert-butylamine or isopropylamine in a 1:3 molar ratio leads to the novel iminomethylene phosphanes F3CP=C=N(tBu) [(2), 30% yield] and F3CP=C=N(iPr) [(3), 5%], respectively. 2 slowly decomposes at room temperature giving tert-butylisonitrile and the cyclophosphanes (F3CP)n (n = 3, 4, 5). 3 is found to be less stable than 2 and for example is attacked by primary amines. The reaction of 2 with 2,3-dimethyl-1,3-butadiene or trimethylphosphane yields, on the one hand, the cycloaddition product of bis(trifluormethyl)diphosphene (4), and on the other hand, the phosphorus ylid Me3P=PCF3 (5) together with (tBu)NC.2 and 3, respectively, are not obtained from (F3C)2PH and the corresponding primary amines in a series of HF elimination and H2NR addition reactions. The main products formed from a 1:4 molar mixture of (F3C)2PH and H2N(iPr) in a one-pot procedure were shown to be the chiral phosphanes F3CP[NH(iPr)]C[=N(iPr)]H (6), F3CP[NH(iPr)]CHF2 (7) and F3CP[NH(iPr)]CH2F (8) (60:35:5). The corresponding reaction of (F3C)2PH with H2N(tBu) mainly yields the compound F3CP[NH(tBu)]CH2F (10).


2021 ◽  
Vol 72 (3) ◽  
pp. 33-44
Author(s):  
Haifeng Tian ◽  
Yongyong Nan ◽  
Jinlong Lv ◽  
Fei Zha ◽  
Xiaohua Tang ◽  
...  

Directly incorporated phosphorus species into the framework of HZSM-5 zeolite (H[P, Al]-ZSM-5) was successfully synthesized by the facile hydrothermal method. It was characterized by employing XRD, ICP-OES, SEM, FT-IR, N2 adsorption-desorption, NH3-TPD, XPS and TG-DTA, respectively. The effects of the phosphorus species content, temperature, WHSV, and the molar ratio of methanol/1-butene in coupling transformation of methanol with 1-butene to propylene catalyzed by H[P, Al]-ZSM-5 in a fixed bed reactor were studied systematically. Tests have suggested the acid content and specific surface area of H[P, Al]-ZSM-5 are reduced. Under the condition of reaction temperature at 550�Z, molar ratio of methanol/1-butene to 1.0, reaction pressure at 0.1 MPa and WHSV= 3.53 h-1, the P-modified HZSM-5 zeolite (with the P2O5 molar composition of 0.4 )the selectivity and yield of propylene are 35.6% and 32.5%, respectively.


2017 ◽  
Vol 25 (2) ◽  
pp. 163-178 ◽  
Author(s):  
Reza Heydari ◽  
Rohollah Rahimi ◽  
Mehrnoosh Kangani ◽  
Afshin Yazdani-Elah-Abadi ◽  
Mojtaba Lashkari

Abstract The potassium carbonate was applied as a green and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic systems, via the condensation between aromatic aldehydes, malononitrile and dimedone/1-naphtole by a grinding method at room temperature and solvent-free conditions. Short reaction times, environmentally friendly procedure and excellent yields are the main advantages of this procedure which makes it more economic than other environmentally synthetic methods.


2013 ◽  
Vol 66 (2) ◽  
pp. 262 ◽  
Author(s):  
Guo-Feng Chen ◽  
Hai-Dong Shen ◽  
Hui-Ming Jia ◽  
Li-Yan Zhang ◽  
Hong-Yan Kang ◽  
...  

A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.


2012 ◽  
Vol 9 (4) ◽  
pp. 2322-2331 ◽  
Author(s):  
Abdolkarim Zare

A highly efficient protocol for the one-pot multi-component condensation of acetophenones with aromatic aldehydes, acetonitrile and acetyl chloride in the presence of melamine trisulfonic acid (MTSA) as a highly efficient and recyclable sulfonic acid-containing catalyst at room temperature is described. In this method, β-acetamido ketone derivatives are obtained in high to excellent yields and in relatively short reaction times.


2017 ◽  
Vol 12 (2) ◽  
pp. 25 ◽  
Author(s):  
Aamer Saeed ◽  
Danish Shahzad ◽  
Fayaz Ali Larik ◽  
Pervaiz Ali Channar ◽  
Haroon Mahfooz ◽  
...  

<p>A series of 4-aryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyri-dines 6a-6h were prepared by using the one-pot three component synthetic method. The target compounds 6a-6h were synthesized by reacting two molar equivalents of ketone functionality and one mole of aromatic aldehydes in ammonium acetate to obtain the desired products. The structures of newly synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. All the synthesized compounds were screened for their elastase inhibition and antioxidant activity. Almost all of the com-pounds 6a-h showed good to excellent activities against elastase enzyme more than the reference drug. Compounds 6d and 6b at 0.2 ± 0.0 µM and 0.2 ± 0.0 µM were found to most potent derivatives against elastase enzyme. Compound 6a exhibited prominent free radical scavenging activity. From the results of the biological activity, we infer that some derivatives can serve as lead molecules in pharmacology.</p><p><strong>Video Clip of Methodology</strong>:</p><p>3 min 13 sec   <a href="https://youtube.com/v/gPLdpGpZhR8">Full Screen</a>   <a href="https://youtube.com/watch?v=gPLdpGpZhR8">Alternate</a></p>


2018 ◽  
Vol 90 (2) ◽  
pp. 387-394 ◽  
Author(s):  
Ali Maleki ◽  
Mina Ghassemi ◽  
Razieh Firouzi-Haji

Abstract In this work, an efficient chitosan-based magnetic bionanocomposite was synthesized via a two-step method and characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermo gravimetric analysis (TGA), energy-dispersive X-ray (EDX) analysis and scanning electron microscopy (SEM) images. Then, it was used as a heterogeneous catalyst for the one-pot multicomponent syntheses of a variety of heterocyclic compounds including 2-amino-4H-pyrans, 2-amino-4H-chromens and polyhydroquinoline derivatives in ethanol at room temperature. The catalyst was simply separated from the reaction mixture by an external magnet and reused several times. The products were isolated from the reaction mixtures, without any need of column chromatography, in high-to-excellent yields. A reusable and easily recoverable catalyst, use of a green solvent, room temperature and mild reaction conditions are some advantages of the present work.


2018 ◽  
Author(s):  
Huong T. D. Nguyen ◽  
Y B. N. Tran ◽  
Hung N. Nguyen ◽  
Tranh C. Nguyen ◽  
Felipe Gándara ◽  
...  

<p>Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO<sub>2</sub> (low pressure, at room temperature) and moderate CO<sub>2</sub> selectivity over N<sub>2</sub> and CH<sub>4</sub>. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO<sub>2</sub> from binary mixture containing N<sub>2</sub> and CO<sub>2</sub> was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO<sub>2</sub> under mild conditions (1 atm CO<sub>2</sub>, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%). </p><br>


2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.


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