scholarly journals Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst

SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki
Keyword(s):  
Room Temperature ◽  
Significant Loss ◽  
Copper Ferrite ◽  
Multicomponent Synthesis ◽  
Thermo Gravimetric ◽  
Sem Images ◽  
One Pot ◽  
Three Component Reaction ◽  
Ft Ir ◽  
The One

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.

Green multicomponent synthesis of four different classes of six-membered N-containing and O-containing heterocycles catalyzed by an efficient chitosan-based magnetic bionanocomposite

2018 ◽  
Vol 90 (2) ◽  
pp. 387-394 ◽  
Author(s):  
Ali Maleki ◽  
Mina Ghassemi ◽  
Razieh Firouzi-Haji
Keyword(s):  
Room Temperature ◽  
Thermo Gravimetric Analysis ◽  
Gravimetric Analysis ◽  
Multicomponent Synthesis ◽  
Step Method ◽  
Sem Images ◽  
One Pot ◽  
Recoverable Catalyst ◽  
Ft Ir ◽  
The One

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.

Silica sulfuric acid magnetic nanoparticle: an efficient and ecofriendly catalyst for synthesis of spiro[2-amino-4H-pyran-oxindole]s

2015 ◽  
Vol 93 (5) ◽  
pp. 546-549 ◽  
Author(s):  
Ali Reza Karimi ◽  
Meysam Sourinia ◽  
Zeinab Dalirnasab ◽  
Marzie Karimi
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Nanoparticle ◽  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Silica sulfuric acid magnetic nanoparticles efficiently catalyze the one-pot, three-component reaction of isatins and malononitrile with dimedone, 1,3-dimethylbarbituric acid or 4-hydroxycoumarin in EtOH–H2O to afford the corresponding spiro[2-amino-4H-pyran-oxindole] derivatives in high yields under ultrasound irradiation at 60 °C. The heterogeneous nanocatalyst could be recovered easily from the reaction mixture using an external magnet and reused many times without significant loss of its catalytic activity.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature

RSC Advances ◽  
2015 ◽  
Vol 5 (49) ◽  
pp. 39263-39269 ◽  
Author(s):  
Goutam Brahmachari ◽  
Bubun Banerjee
Keyword(s):  
Ammonium Nitrate ◽  
Room Temperature ◽  
Aqueous Ethanol ◽  
Ceric Ammonium Nitrate ◽  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One

Ceric ammonium nitrate (CAN)-catalyzed one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (3a–3u) has been developed via a pseudo three-component reaction in aqueous ethanol at room temperature.

An Efficient One Pot, Multicomponent Synthesis of 1, 3-Thiazolidin-4-Ones Using L-Proline as Catalyst in Water

2021 ◽  
Vol 18 ◽  
Author(s):  
Yatin U. Gadkari ◽  
Rajesh D. Shanbhag ◽  
Vikas N. Telvekar
Keyword(s):  
Energy Efficient ◽  
Room Temperature ◽  
Thioglycolic Acid ◽  
Current Approach ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
The One ◽  
Aqueous Conditions ◽  
Aromatic Heterocyclic

: An efficient methodology for the synthesis of 1,3-thiazolidin-4-ones using L-Proline as catalyst under aqueous conditions has been developed. The one-pot, multicomponent reaction of aromatic/heterocyclic aldehyde, aromatic amine and thioglycolic acid at room temperature give 1,3-thiazolidin-4-ones in moderate to good yields. Further, the current approach is notably greener than traditional methods with E-factor of 3.1 and the eco scale score of 96. The developed protocol offers several features, such as being simple, environmentally benign, energy-efficient, economical, mild conditions, shorter reaction time.

One-pot Multicomponent Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1, 2-a]pyrazines in Water Catalyzed by Fe3O4@SiO2@L-Arginine-SA Magnetic Nanoparticles

2020 ◽  
Vol 17 (6) ◽  
pp. 473-482
Author(s):  
Hedieh Rostami ◽  
Lotfi Shiri
Keyword(s):  
Magnetic Nanoparticles ◽  
Column Chromatography ◽  
Room Temperature ◽  
Green Solvent ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
Derivatives Of ◽  
Green Conditions

Aims: Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines using magnetic nanoparticles. Background: One-pot, three component reaction for the synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines is reported. For the synthesis of pyrrolo[1,2-d][1,4]benzoxazines use of 2- aminophenols, dialkylacetylenedicarboxylates and β -nitrostyrene derivatives and Pyrrolo[1,2-a]pyrazines synthesized from reaction of ethylenediamine, dialkylacetylenedicarboxylates and β-nitrostyrene derivatives is discussed. Materials and Methods: 2-aminophenol (0.5 mmol) and dimethylacetylenedicarboxylate (0.5 mmol) in water (3 ml) were stirred at room temperature for 10 min. Then, β-nitrostyrene (0.5 mmol) and Fe3O4@SiO2@LArginine- SA MNPs (0.07 g) were added and the mixture was refluxed for 5 h. After completion of the reaction, the mixture was cooled to room temperature and the catalyst was separated with external magnet and product extracted with dichloromethane. More purification of products was performed by column chromatography (nhexane/ ethyl acetate 4:1). Ethylenediamine (0.6 mmol) was added to dialkylacetylenedicarboxylate (0.6 mmol) in 3 ml water and was stirred for 10 min at room temperature. Later, β -nitrostyrene (0.5 mmol) and Fe3O4@SiO2@L-Arginine-SA MNPs (0.06 g) were added to mixture reaction and refluxed for 3 h. After completion, the mixture reaction was cooled to room temperature and the catalyst was separated by an external magnet. Then, the product was extracted with dichloromethane. For more purification column chromatography was used (n-hexane/ethylacetate 1:1). Results and Discussion: In this research, we have synthesized new derivatives of pyrrolo[1,2- d][1.4]benzoxazines and pyrrolo[1,2-a]pyrazines in green conditions consisting of use of water as a green solvent and magnetic nanoparticles. Conclusion: In this research, we have synthesized new derivatives of pyrrolo[1,2-d][1.4]benzoxazines and pyrrolo[1,2-a]pyrazines in green conditions consisting of use of water as a green solvent and magnetic nanoparticles which were easily separated from mixture with an external magnet and had the capability to be recovered and reused. Also, in this work, the yield was good and the time of reactions was low compared with prior research.

A Clean, Benign, Energy Efficient One-Pot Multicomponent Synthesis and Bio-evaluation of Novel [1,2,4]Triazolo[1,5-a]quinolines

2021 ◽  
Vol 6 (2) ◽  
pp. 111-115
Author(s):  
H.P. Parekh ◽  
M.H. Chauhan ◽  
N.L. Solanki ◽  
V.H. Shah
Keyword(s):  
Room Temperature ◽  
Cost Effective ◽  
Second Step ◽  
Mass Spectral Data ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Green Catalyst ◽  
Mass Spectral ◽  
Elemental Analyses ◽  
Ft Ir

In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.

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 ◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Molar Ratio ◽  
Green Solvents ◽  
N2 Adsorption ◽  
One Pot ◽  
Ft Ir ◽  
The One ◽  
Adsorption Desorption

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.

scholarly journals Study on the Synthesis of Some (Un)Substituted 2-Amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles in the Water Medium

Proceedings ◽  
2018 ◽  
Vol 9 (1) ◽  
pp. 67
Author(s):  
Nguyen Dinh Thanh ◽  
Do Son Hai ◽  
Pham Thi Thu Hien ◽  
Vu Thi Ngoc Bich ◽  
Vu Ngoc Toan ◽  
...  
Keyword(s):  
Sodium Carbonate ◽  
Room Temperature ◽  
Sodium Carbonate Solution ◽  
Carbonate Solution ◽  
Simple Synthesis ◽  
Water Medium ◽  
One Pot ◽  
Three Component Reaction ◽  
Substituted Benzaldehydes ◽  
The One

An efficient and simple synthesis of substituted 2-amino-4H-chromene-3-carbonitriles was developed by the one-pot and three-component reaction of a mixture of corresponding substituted benzaldehydes, resorcinol, and malononitrile in the presence of sodium carbonate solution as a catalyst at room temperature.

Ultrasonic Assisted Synthesis of 2, 3-Dihydroquinazolin-4(1H)-ones Involving Three-Component Reaction of Isatoic Anhydride, Amines and Pyrazole Carbaldehydes Catalyzed by [γ-Fe2O3@HAp-SO3H]

2019 ◽  
Vol 17 (1) ◽  
pp. 24-30
Author(s):  
Kiana F. Sina ◽  
Asieh Yahyazadeh ◽  
Nosrat O. Mahmoodi ◽  
Kurosh R. Moghadam ◽  
Mohammad Nikpassand ◽  
...  
Keyword(s):  
Reaction Times ◽  
Isatoic Anhydride ◽  
Bacterial Strains ◽  
One Pot ◽  
Three Component Reaction ◽  
Ultrasonic Assisted ◽  
Ft Ir ◽  
Novel Method ◽  
The One ◽  
Work Up

The combination of [γ-Fe2O3@HAp-SO3H] as a catalyst and ultrasonic effect catalyzed the synthesis of diverse derivatives of 2, 3-dihydroquinazolin-4(1H)-ones which is reported in this study. The products were synthesized via the one-pot three-component reaction of isatoic anhydride, amines and pyrazole carbaldehydes in water: EtOH catalyzed by recoverable [γ-Fe2O3@HAp-SO3H]. This paper conducted an investigation of the effect of various solvents, temperatures and catalysts on the reactions. Short reaction times, mild reaction conditions, simple work-up, the desired yields and the use of an appropriate catalyst are the advantages of this novel method. The new derivatives were validated by using FT-IR, 1HNMR, and 13CNMR. Moreover, the synthesized compounds were screened for their antimicrobial activity against bacterial strains.

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