Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate as an efficient and reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidones under solvent-free conditions

2011 ◽  
Vol 65 (6) ◽  
Author(s):  
Xin-Bin Yang ◽  
Xiang-Kai Fu ◽  
Yu Huang ◽  
Ren-Quan Zeng
Keyword(s):  
Catalytic Activity ◽  
Elemental Analysis ◽  
Biginelli Reaction ◽  
Significant Loss ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Simple Filtration

AbstractZirconium(IV) 4-sulphophenylethyliminobismethylphosphonate (ZSBEDP) was prepared and characterised by elemental analysis, IR, TG-DSC, and XRD. ZSBEDP was found to be an efficient catalyst for the Biginelli reaction of aromatic aldehyde, ethyl acetoacetate, and urea or thiourea under solvent-free conditions so as to give 3,4-dihydropyrimidones in good to excellent yields. The catalyst can be separated by simple filtration and reused without significant loss of its catalytic activity.

Commercial ZrO2 as a new, efficient, and reusable catalyst for the one-step synthesis of quinolines in solvent-free conditions

2009 ◽  
Vol 87 (8) ◽  
pp. 1122-1126 ◽  
Author(s):  
Mona Hosseini-Sarvari
Keyword(s):  
Catalytic Activity ◽  
Carbonyl Compound ◽  
Significant Loss ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
One Step ◽  
The One ◽  
High Yields

Commercially available zirconia (ZrO2) is reported as an extremely efficient catalyst for the synthesis of quinolines. A one-step reaction of 2-aminoarylketones and a carbonyl compound (Friedlander reaction) took place under solvent-free conditions to afford the corresponding quinolines in good-to-high yields in the presence of ZrO2. Furthermore, the catalyst is reused several times without any significant loss of its catalytic activity.

scholarly journals One-pot three-component tandem annulation of 4-hydroxycoumarine with aldehyde and aromatic amines using graphene oxide as an efficient catalyst

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Rabindranath Singha ◽  
Aminul Islam ◽  
Pranab Ghosh
Keyword(s):  
Graphene Oxide ◽  
Catalytic Activity ◽  
Aromatic Amines ◽  
Significant Loss ◽  
Solvent Free ◽  
One Pot ◽  
Efficient Catalyst ◽  
New Class ◽  
Broad Scope ◽  
Plausible Mechanism

AbstractA convenient and efficient solvent-free, facile, one-pot three-component graphene oxide catalysed approach has been described for the synthesis of chromeno-[4,3-b]quinolin-6-one derivatives from 4-hydroxycoumarin with aldehydes and aromatic amines. Graphene oxide (GO) has proved to be a new class of heterogeneous carbocatalyst which could be easily recovered and reused up to 5th run without significant loss of its catalytic activity. A broad scope of substrate applicability is offered and a plausible mechanism is also suggested for this developed protocol.

scholarly journals Al(NO3)3 · 9H2O: An Efficient Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Both under Reflux or Solvent-Free Conditions

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Eskandar Kolvari ◽  
Maryam Mirzaeeyan
Keyword(s):  
Low Cost ◽  
Biginelli Reaction ◽  
Acid Catalyst ◽  
Solvent Free ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Environmentally Friendly Process

Al(NO3)3 · 9H2O efficiently catalyzes the three-component Biginelli reaction between an aldehyde, aβ-dicarbonyl compound, and urea or thiourea in refluxing ethanol and solvent-free (SF) conditions to afford the corresponding dihydropyrimidinones in high yields. The advantages of this method involve the easy procedure, the environmentally friendly process, and the low cost of the Lewis acid catalyst.

scholarly journals H4SiW12O40Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a] Xanthen-11-ones Under Solvent-Free Conditions

2012 ◽  
Vol 9 (2) ◽  
pp. 786-790 ◽  
Author(s):  
A. Hassankhani ◽  
E. Mosaddegh ◽  
S. Y. Ebrahimipour
Keyword(s):  
Catalytic Activity ◽  
Solvent Free ◽  
Environmentally Benign ◽  
Reusable Catalyst ◽  
High Catalytic Activity ◽  
One Pot ◽  
Aryl Aldehydes ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
The One

An efficient and environmentally benign protocol for the one-pot, three-component synthesis of 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one derivatives by condensation of aryl aldehydes, 2-naphthol and dimedone using H4SiW12O40(SiWA) as a reusable catalyst with high catalytic activity was reported. The reaction was carried out at 100 ºC under solvent-free conditions within 15-40 min in 82-91% yield.

scholarly journals An Efficient One-Pot Synthesis of 1,8-Dioxodecahydroacridines Using Silica-Supported Polyphosphoric Acid (PPA-SiO2) under Solvent-Free Conditions

2012 ◽  
Vol 9 (2) ◽  
pp. 504-509 ◽  
Author(s):  
Farid Moeinpour ◽  
Amir Khojastehnezhad
Keyword(s):  
Polyphosphoric Acid ◽  
Ammonium Acetate ◽  
Significant Loss ◽  
One Pot ◽  
Efficient Catalyst ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions ◽  
Short Period ◽  
Simple Filtration ◽  
High Yields

Silica gel–supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the synthesis of 1,8-dioxodecahydroacridines via one-pot three-component condensation of aryl aldehydes, dimedone, and ammonium acetate or 4-methyl aniline in high yields, easy workup procedure and short period of times. The catalyst was separated by simple filtration and used in the reaction three times without any significant loss of its activity.

Sulfonic Acid-Functionalized Magnetic Nanoparticles as an Efficient Catalyst for the Synthesis of Benzo[4, 5]imidazo[1, 2-a]pyrimidine Derivatives, 2-Aminobenzothia Zolomethylnaphthols and 1-Amidoalkyl-2-naphthols

2019 ◽  
Vol 16 (7) ◽  
pp. 1040-1054
Author(s):  
Fatemeh K. Damghani ◽  
Seied A. Pourmousavi ◽  
Hamzeh Kiyani
Keyword(s):  
Catalytic Activity ◽  
Magnetic Separation ◽  
Low Cost ◽  
Solvent Free ◽  
High Catalytic Activity ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Nano Catalysts

Background: Carbon-based sulfonated catalysts have several advantages but their separation by filtration is still a challenge. On the other hand, the synthesis of magnetic sulfonated carbon nanoparticle indicated that the magnetic separation could be an efficient way to separate the catalyst from the reaction mixture. Objective: In order to synthesize a separable magnetic Fe3O4@C-SO3H nanoparticle (MNPs) with high catalytic activity in organic transformation, three environmental-benign and low-cost sulfonic acidfunctionalized magnetic nanoparticle (Fe3O4@C-SO3H) were successfully synthesized. Materials and Methods: The Nano catalysts were prepared by solvothermal carbonization of Sucrose (Suc), Starch (Sta) or Cellulose (Cel) in the presence of Fe3O4 Nanoparticle and then grafting of the sulfonic groups on the surface of resulted Fe3O4@C nanoparticles in the presence of p-Toluenesulfonic. Then the Nano catalysts were characterized using XRD, FESEM and FT-IR. Results: Three Fe3O4@C-SO3H were successfully synthesized. The resulted MNPs were used for the synthesis of benzo [4, 5] imidazo[1, 2-a]-pyrimidine derivatives, 2/-aminobenzothiazolomethylnaphthols and 1-amidoalkyl-2-naphthols under solvent-free conditions in excellent yields. It was found that high catalytic activity and easy magnetic separation from the reaction mixture are important achievement with regard to the efficiency and reusability of the catalyst in synthesis. Conclusion: The MNPs were synthesized and used as an efficient catalysts for the one-pot synthesis of benzo [4, 5] imidazo[1, 2-a]-pyrimidine derivatives, 2/-aminobenzothiazolomethylnaphthols, and 1-amidoalkyl-2- naphthols under solvent-free conditions in excellent yields. High catalytic activity and easy magnetic separation from the reaction mixture are two factors for evaluating the performance of Fe3O4@C-SO3H nanoparticles in the organic transformations.

Preparation and Characterization of a Novel Room Temperature Dicationic Ionic Liquid and its Application in the Synthesis of Xanthenediones Under Solvent-Free Conditions

2018 ◽  
Vol 21 (8) ◽  
pp. 602-608 ◽  
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Significant Loss ◽  
Solvent Free ◽  
Acidity Function ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Hammett Acidity Function ◽  
Dicationic Ionic Liquid

Aim and Objective: In the present work, 1, 1’-sulfinyldiethylammonium bis (hydrogen sulfate) as a novel room temperature dicationic ionic liquid was synthesized and used as a catalyst for xanthenediones synthesis. Material and Method: The dicationic ionic liquid has been synthesized using ethylamine and thionyl chloride as precursors. Then, by the reaction of [(EtNH2)2SO]Cl2 with H2SO4, [(EtNH2)2SO][HSO4]2 was prepared and after that, it was characterized by FT-IR, 1H NMR, 13C NMR as well as Hammett acidity function. This dicationic ionic liquid was used as a catalyst for the synthesis of xanthenediones via condensation of structurally diverse aldehydes and dimedone under solvent-free conditions. The progress of the reaction was monitored by thin layer chromatography (ethyl acetate/n-hexane = 3/7). Results: An efficient solvent-free method for the synthesis of xanthenediones has been developed in the presence of [(EtNH2)2SO][HSO4]2 as a powerful catalyst with high to excellent yields, and short reaction times. Additionally, recycling studies have demonstrated that the dicationic ionic liquid can be readily recovered and reused at least four times without significant loss of its catalytic activity. Conclusion: This new dicationic ionic liquid can act as a highly efficient catalyst for xanthenediones synthesis under solvent-free conditions.

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

Synthesis of Dihydropyrimidinones (DHPMs) and Hexahydro Xanthene Catalyzed by 1,4-Diazabicyclo [2.2.2] Octane Triflate Under Solvent-Free Condition

2019 ◽  
Vol 16 (5) ◽  
pp. 776-786 ◽  
Author(s):  
Deepa ◽  
Geeta D. Yadav ◽  
Mohd J. Aalam ◽  
Pooja Chaudhary ◽  
Surendra Singh
Keyword(s):  
Ethyl Acetoacetate ◽  
Biginelli Reaction ◽  
Solvent Free ◽  
Efficient Catalyst ◽  
Solvent Free Condition ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives ◽  
Different Temperatures ◽  
Flash Column Chromatography ◽  
Biginelli Condensation

Objective:DABCO salts were evaluated as catalysts for the Biginelli reaction between 4- methoxybenzaldehyde, urea and ethyl acetoacetate under solvent-free conditions. 1,4-Diazabicyclo [2.2.2] octane triflate was found to be a simple, inexpensive, highly efficient catalyst for Biginelli reaction for a variety aromatic aldehyde with urea and ethyl acetoacetate at 80°C afforded corresponding 3,4-dihydropyrimidinones in 50-99% yields after 30-120 minutes. 1,3-Cyclohexadione was used in place of ethyl acetoacetate in the absence of urea this methodology is giving hexahydro xanthene derivatives in good to excellent yields after 3-4 hours.Methods:DABCO salt 4 (5 mol%), 4-methoxybenzaldehyde (0.73 mmol) and urea (0.73 mmol) were stirred for 10 minutes at 80°C, then ethyl acetoacetate (1.5 equiv.) was added and reaction mixture was stirred at 80°C for specified time. The resulting solution was stirred continuously and progress of the reaction was followed by TLC. The crude reaction mixture was purified by flash column chromatography on silica gel (hexane/ethyl acetate (1:2)) to give pure desired product.Results:Reaction conditions of the Biginelli reaction were optimized using 4-methoxybenzaldehyde (0.73 mmol), urea (0.73 mmol), and ethyl acetoacetate (5 equiv.) as model substrates catalyzed by 1,4-Diazabicyclo [2.2.2] octane triflate (5 mol%) in a different solvents, screening of different catalysts and different temperatures. Neat condition was found to be the best for the Biginelli condensation and corresponding 3,4- dihydropyrimidinones was obtained in good to excellent yields. When the reaction was carried out with benzaldehyde derivatives and cyclohexane-1,3-dione in place of ethyl acetoacetate in the absence of urea, solely corresponding hexahydro xanthene derivatives were obtained in 61-91% yields.Conclusion:In conclusion, we have applied salts of 1,4-Diaza-bicyclo [2.2.2] octane as catalysts in the Biginelli condensation and corresponding 3,4-dihydropyrimidinones were obtained in 50- 99% yields under solvent free conditions. This methodology is having advantages like simple work-up; low loading of catalyst and reaction was performed at moderate temperature under solvent-free conditions.

Sign in / Sign up

Export Citation Format

Share Document