One-pot preparation of β-amido ketones/esters in a three-component condensation reaction using magnesium hydrogensulfate as an effective and reusable catalyst

2008 ◽  
Vol 86 (5) ◽  
pp. 376-383 ◽  
Author(s):  
Hamid Reza Shaterian ◽  
Asghar Hosseinian ◽  
Majid Ghashang
Keyword(s):  
Room Temperature ◽  
Acetyl Chloride ◽  
Condensation Reaction ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Green Catalyst ◽  
Mild Conditions ◽  
Aryl Aldehyde ◽  
Ketone Ester

A one-pot, three-component condensation of an aryl aldehyde, an enolizable ketone or β-keto ester, acetyl chloride, and acetonitrile or benzonitrile in the presence of magnesium hydrogensulfate as an active, recoverable, and reusable green catalyst is described for the synthesis of β-amido ketones/esters at room temperature. The key features of this methodology are simplicity, mild reaction conditions, and high to excellent yields.Key words: multi-component reaction, magnesium hydrogensulfate, heterogeneous catalyst, β-amido ketone/ester, mild conditions.

Nano-TiO2: an Eco-friendly and Re-usable Catalyst for the One-pot Synthesis of β-Acetamido Ketones

2009 ◽  
Vol 64 (3) ◽  
pp. 347-350 ◽  
Author(s):  
Bi Bi Fatemeh Mirjalili ◽  
Ali Akbari
Keyword(s):  
Room Temperature ◽  
Acetyl Chloride ◽  
Reusable Catalyst ◽  
Nano Tio2 ◽  
One Pot ◽  
One Pot Synthesis ◽  
Aryl Aldehyde ◽  
The One ◽  
Aryl Ketone

Nano-TiO2 as an efficient, eco-friendly and reusable catalyst was applied for the one-pot synthesis of β -acetamido ketones. In this improved procedure, an aryl aldehyde, an aryl ketone, acetyl chloride and acetonitrile were condensed in the presence of the catalyst at room temperature.

scholarly journals Application of One-Pot Three-Component Condensation Reaction for the Synthesis of New Organophosphorus–Sulfur Macrocycles

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1496-1501 ◽  
Author(s):  
J. Woollins ◽  
Guoxiong Hua ◽  
David Cordes ◽  
Alexandra Slawin
Keyword(s):  
Multicomponent Reaction ◽  
Room Temperature ◽  
Condensation Reaction ◽  
Synthesis Method ◽  
Membered Ring ◽  
One Pot ◽  
X Ray ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Sulfur Heterocycles

An efficient approach has been developed for the synthesis of new phosphorus–sulfur heterocycles by a one-pot three-component condensation reaction of a four-membered-ring thionation reagent [Lawesson’s reagent or its ferrocene analogue (2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide)], an alkane- or arenedithiol, and a dihaloalkane at room temperature in the presence of triethylamine. The simple synthesis method with mild conditions (room temperature and normal reactant concentrations) enhances further the application of the multicomponent reaction in the preparation of novel phosphorus–sulfur heterocycles. Six representative X-ray structures confirmed the formation of these macrocycles.

scholarly journals One-Pot Synthesis ofβ-Acetamido Ketones Using Boric Acid at Room Temperature

2012 ◽  
Vol 2012 ◽  
pp. 1-4 ◽  
Author(s):  
Zahed Karimi-Jaberi ◽  
Korosh Mohammadi
Keyword(s):  
Boric Acid ◽  
Room Temperature ◽  
Simple Procedure ◽  
Condensation Reaction ◽  
Solid Acid Catalyst ◽  
Reaction Times ◽  
Acid Catalyst ◽  
One Pot ◽  
Green Catalyst ◽  
One Pot Condensation

β-acetamido ketones were synthesized in excellent yields through one-pot condensation reaction of aldehydes, acetophenones, acetyl chloride, and acetonitrile in the presence of boric acid as a solid heterogeneous catalyst at room temperature. It is the first successful report of boric acid that has been used as solid acid catalyst for the preparation ofβ-acetamido ketones. The remarkable advantages offered by this method are green catalyst, mild reaction conditions, simple procedure, short reaction times, and good-to-excellent yields of products.

scholarly journals Melamine Trisulfonic Acid as a Highly Efficient and Reusable Catalyst for the Synthesis of β-Acetamido Ketones

2012 ◽  
Vol 9 (4) ◽  
pp. 2322-2331 ◽  
Author(s):  
Abdolkarim Zare
Keyword(s):  
Sulfonic Acid ◽  
Room Temperature ◽  
Acetyl Chloride ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Reusable Catalyst ◽  
One Pot ◽  
Highly Efficient ◽  
The One ◽  
Melamine Trisulfonic Acid

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.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

DFT Study and Synthesis of Novel Bioactive Bispyrazole Using Mg/AlLDH as a Solid Base Catalyst

2020 ◽  
Vol 14 ◽  
Author(s):  
Soufiane Akhramez ◽  
Youness Achour ◽  
Mustapha Diba ◽  
Lahoucine Bahsis ◽  
Hajiba Ouchetto ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Experimental Finding ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Mechanistic Study ◽  
Knoevenagel Reaction ◽  
Solid Base ◽  
Reaction Conditions ◽  
Aryl Aldehyde

Background: In this study, an efficient synthesis of novel bispyrazole heterocyclic molecules by condensation of substituted aromatic aldehydes with 1,3-diketo-N-phenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst is reported. The attractive features of this protocol are as follows: mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Methods: The bispyrazole derivatives 3a-m were prepared by condensation reaction of substituted aromatic aldehydes with 1,3-diketo-Nphenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst under THF solvent at the refluxing temperature. Objective: To synthesize a novel bispyrazole heterocyclic molecule may be have important biological activities and thus can be good candidates for pharmaceutical applications. Results: This protocol describes the Synthesis of Bioactive Compounds under mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Conclusion: In summary, the pharmacologically interesting bis-pyrazole derivatives have been synthesized through Mg/Al-LDH as a solid base catalyst, in THF as solvent. Thus, the synthesized bioactive compounds containing the pyrazole ring may be have important biological activities and thus can be good candidates for pharmaceutical applications. Therefore, the catalyst Mg/Al-LDH showed high catalytic activity. Besides, a series of bispyrazole molecules were synthesized with a good yield and easy separation of the catalyst by simple filtration. Moreover, DFT calculations and reactivity indexes are used to explain the selectivity of the condensation reaction between aryl benzaldehyde and 1,3-diketo-Nphenylpyrazole via Knoevenagel reaction, and the results are in good agreement with the experimental finding.

One-pot multicomponent synthesis of highly functionalized bio-active pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives using ZrO2 nanoparticles as a reusable catalyst

2015 ◽  
Vol 17 (5) ◽  
pp. 2859-2866 ◽  
Author(s):  
Arijit Saha ◽  
Soumen Payra ◽  
Subhash Banerjee
Keyword(s):  
Room Temperature ◽  
Zro2 Nanoparticles ◽  
Reusable Catalyst ◽  
Coumarin Derivatives ◽  
Multicomponent Synthesis ◽  
One Pot

Herein, a facile one-pot multicomponent protocol for the synthesis of biologically important pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been demonstrated using ZrO2 nanoparticles as reusable catalyst at room temperature.

An efficient multicomponent, one-pot synthesis of Betti bases catalyzed by cerium (IV) ammonium nitrate (CAN) at ambient temperature

2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Ambient Temperature ◽  
Environmental Pollution ◽  
Ammonium Nitrate ◽  
Room Temperature ◽  
Catalytic Amount ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Work Up ◽  
Cerium Iv Ammonium Nitrate

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.

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