One-pot Three-component Condensation Reaction Research Articles

Design, preparation and characterization of urea-functionalized Fe3O4/SiO2 magnetic nanocatalyst and application for the one-pot multicomponent synthesis of substituted imidazole derivatives

Novel urea-functionalized silica-based magnetite hybrid core-shell nanoparticles were prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), scanning electron microscopy (SEM), X-ray diffraction (XRD) and vibrating sample magnetometer (VSM) analyses. It was used as a highly efficient and recoverable heterogeneous nanocatalyst for the one-pot three-component condensation reaction between benzil or benzoin with various substituted aldehydes and ammonium acetate to afford the corresponding imidazoles under mild reaction conditions in high-to-quantitative yields. The catalyst was recycled at least five times without significant decrease in the catalytic activity.

A metal-free tandem C-C/C-O bond formation approach to densely functionalized indolyl 4H-chromenes catalyzed by polystyrene-supported p-toluenesulfonic acid under solvent-free conditions.

A new environmentally benign and highly convergent protocol for the synthesis of indolyl 4H-chromene derivatives has been developed. This one-pot three-component condensation reaction of salicylaldehyde, cyclic 1,3-diketones, and indole is promoted by PS-PTSA as a reusable heterogeneous acid catalyst under solvent-free conditions. This protocol demonstrates several notable advantages such as that the catalyst is readily available and can be recovered and reused for at least five runs without any significant impact on product yields, high atom economy, excellent yields, and efficiency of producing three new bonds (two C-C and one C-O) and one stereo center in a single operation.

A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl3/SiO2 nanoparticles as robust and efficient catalyst

Abstract A simple and green method has been developed for the synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters through a one-pot three-component condensation reaction of primary amines, ethyl acetoacetate and chalcones using FeCl3/SiO2 nanoparticles in ethanol. This method has several advantages such as high to excellent product yields in short time, using an inexpensive and reusable catalyst and available starting material.

SO3H-functionalized mesoporous silica materials as solid acid catalyst for facile and solvent-free synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-trione derivatives

SO3H-functionalized mesoporous silica materials were used to synthesize 2H-indazolo[2,1-b]phthalazine-1,6,11-trione derivatives in a one-pot three-component condensation reaction.

Immobilized silver on surface-modified ZnO nanoparticles: As an efficient catalyst for synthesis of propargylamines in water

Silver nanoparticles were immobilized on ionic liquid modified zinc oxide nanoparticles leading to a ZnO-IL/Ag NPs catalyst, which exhibits high catalytic performance in the synthesis of propargylamines through one-pot three-component condensation reaction of aldehydes, amines, and alkynes in water. The as-prepared catalyst was characterized by ICP-AES, FT-IR, XRD, SEM, and TEM. The catalyst was easily recycled and reused at least five times without significant loss of its catalytic activity.

Synthesis and characterization of a novel paramagnetic functionalized ionic liquid as a highly efficient catalyst in one-pot synthesis of 1-amidoalkyl-2-naphtols

A novel paramagnetic ionic liquid, 3-(2-hydroxyethyl)-1-methyl imidazolium bromotrichloro ferrate (III), was synthesized and exhibited high catalytic performance in the synthesis of 1-amidoalkyl-2-naphthols via one-pot three-component condensation reaction of aromatic aldehydes, 2-naphthol and acetamide at 85°C under solvent-free conditions. The catalyst showed response to an external magnet and was characterized by Fourier transform infrared spectroscopy (FT-IR), UV–Visible spectroscopy, Thermal gravimetric analysis (TGA) and Raman spectroscopy.

Facile synthesis of imidazo[1,2-a]pyridines via a one-pot three-component reaction under solvent-free mechanochemical ball-milling conditions

In this work, 3-aminoimidazo[1,2-a]pyridine derivatives have been synthesized by a one-pot three-component condensation reaction of 2-aminopridines, aldehydes and isocyanides under solvent-free mechanochemical ball-milling conditions in good to excellent yields at room temperature. This efficient protocol has many noticeable advantages such as mild reaction conditions, high yields, high atom economy, short reaction times and simple separation.

One-pot three-component synthesis of some new azo-pyrazoline derivatives

14.00 The starting material azo-benzyloxy acetophenone (2) has been synthesized in three steps; the direct diazotization of p -aminoacetophenone and its coupling reaction with m-cresol gave azo-acetophenone (1), which was benzylated with p -chlorobenzylchloride to give the starting material (2). The later compound was subjected to the one-pot three-component condensation reaction with substituted benzaldehydes and phenylhydrazine in the presence of sodium hydroxide to afford the target molecule azo-pyrazoline derivatives (3a-e) in high yields and short reaction times. The structures of the synthesized compounds were elucidated by using FT-IR, 1 H NMR, 13 C NMR and 13 C DEPT 135 spectra. Normal 0 false false false EN-US X-NONE AR-SA /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Table Normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-priority:99; mso-style-parent:""; mso-padding-alt:0cm 5.4pt 0cm 5.4pt; mso-para-margin:0cm; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Calibri","sans-serif"; mso-bidi-font-family:"Times New Roman";}

Sulfanilic acid: a versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition

A series 1-amidoalkyl-2-naphthols were synthesized by one-pot three-component condensation reaction of β-naphthol with various aromatic aldehydes and amides under thermal (hot plate and oil bath) and microwave techniques. and the effect of various organoacids used as catalyst was studied. Among the various acids screened, p-aminobezene sulphonic acid (sulfanilic acid) came out to be a versatile catalyst and the corresponding products were obtained in good to excellent yield (84–94 %) under solvent-free condition.

Synthesis of new pyran and pyranoquinoline derivatives

Various 2-amino-4H-pyran-3-carbonitriles 1 and 2 were successfully synthesized, via a one-pot three-component condensation reaction of arylaldehyde and malononitrile with methyl acetoacetate and 8-hydroxyquinoline, respectively in moderate yields. These key intermediates 1 and 2 undergo rapid condensation with formic acid and acetic anhydride to give, respectively the corresponding pyranes 3–6 and pyranopyrimidinones 7 and 8. All the synthesized compounds were completely characterized by 1H NMR, 13C NMR, IR and ES-HRMS.

InCl3-catalyzed green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under solvent-free conditions

Abstract A simple, efficient, and green practical approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones from phthalhydrazide, aldehydes, and malononitrile/ethyl cyanoacetate has been developed that uses inexpensive and readily available InCl3 as a catalyst in solvent-free one-pot three-component cyclo condensation reaction. This method should provide high yields, shorter reaction time, easy work-up, purification of products by nonchromatographic method, and cleaner reaction. It is a new strategy for N-fused heterocycles synthesis, which haswider application in organic and medicinal chemistry.

Multi-component reaction on free nano-SiO2 catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability

Nano-SiO2 catalyst was readily prepared from inexpensive starting materials in aqueous media which catalysed the synthesis a-aminophosphonates from aldehydes, amines and diethylphosphate under ultrasonication in water. High catalytic activity and ease of recovery from the reaction mixture using filtration, and reuse without significant losses in performance are additional eco-friendly attributes of this catalytic system. Unsupported ‘free’ nano-SiO2 has been shown to be a stable yet highly active catalyst for preparing a variety of a-aminophosphonates from one-pot three-component condensation reaction.

L-Proline as Reusable and Organo Catalyst for the One-Pot Synthesis of Substituted 2-Amino-4H-Chromenes

L-proline catalyzed one-pot three-component condensation reaction of aromatic aldehydes, malononitrile and naphthols proceeded in EtOH to afford corresponding 2-amino-4H-chromenes in high to excellent yields at reflux conditions. The protocol found to be fairly general and the catalyst was reused in subsequent reactions with consistent activity. Moreover, this method offers several advantages including high to excellent yields of products as well as a simple experimental, work-up procedure and product separation without further purification with column chromatography which makes it a useful and attractive process for the synthesis of these compounds. Keywords: L-proline, Aldehydes, Malononitrile, naphthols, Multi-Component Reaction, chromenes

Synthesis of a new class of tetronic acid derivatives: a one-pot three-component condensation reaction between isoquinoline or pyridine and dialkyl acetylenedicarboxylate with tetronic acid

Reaction of the zwitterions generated from isoquinoline or pyridine and dialkyl acetylenedicarboxylate with tetronic acid leads to 1,2-dihydroisoquinoline or 1,2-dihydropyridine tetronic acid derivatives without using any catalyst or activation at room temperature.

ChemInform Abstract: Synthesis of 3,3‐Disubstituted Oxindoles via a Three‐Component Condensation Reaction in H2O.

An efficient method has been developed for the synthesis of a novel series of unsymmetrically 3,3-disubstituted oxindoles in good-to-high yields by a one-pot three-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, an isatin, and a barbituric acid derivative, in H2O, and with p-toluenesulfonic acid as a catalyst, at 90°. The effects of solvent, temperature, and the amount of catalyst on the yield of the reaction have been investigated. Additionally, the influence of hydrophilicity and hydrophobicity of the reactants on the selectivity of products has been examined.

Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

Synthesis of 3,3‐Disubstituted Oxindoles via a Three‐Component Condensation Reaction in H2O

AbstractAn efficient method has been developed for the synthesis of a novel series of unsymmetrically 3,3‐disubstituted oxindoles in good‐to‐high yields by a one‐pot three‐component condensation reaction of 2‐hydroxynaphthalene‐1,4‐dione, an isatin, and a barbituric acid derivative, in H2O, and with p‐toluenesulfonic acid as a catalyst, at 90°. The effects of solvent, temperature, and the amount of catalyst on the yield of the reaction have been investigated. Additionally, the influence of hydrophilicity and hydrophobicity of the reactants on the selectivity of products has been examined.

Triazine functionalized ordered mesoporous organosilica as a novel organocatalyst for the facile one-pot synthesis of 2-amino-4H-chromenes under solvent-free conditions

A highly ordered 2D-hexagonal mesoporous material functionalized with a triazine moiety has been synthesized via post-synthetic modification of mesoporous SBA-15 with thiols followed by a thiol–ene click reaction using 2,4,6-triallyloxy-1,3,5-triazine. A facile one-pot three-component condensation reaction of aromatic aldehyde, malononitrile and activated phenols for the synthesis of a diverse range of 2-amino-4H-chromenes has been efficiently catalyzed over this novel mesoporous metal-free heterogeneous organocatalyst under solvent-free reaction conditions. Further, this organocatalytic reaction is waste-free, easy to work-up and efficiently reused. The organic products have been isolated from the reaction mixture by using easily disposable solvents and can be easily purified by re-crystallization.

A facile green synthesis and in vitro antimicrobial activity 4H-pyrimido[2,1-b][1,3]benzothiazole derivatives using aluminum trichloride under solvent free conditions

Aluminum trichloride acts as readily available, inexpensive, and efficient catalyst for one-pot three-component condensation reaction of aldehydes, dicarbonyl, and 2-amino benzothiazole under the solvent-free conditions to afford the 4H-pyrimido[2,1-b][1,3]benzothiazole derivatives 4 with good yield. The compounds synthesized in this study were evaluated for their antibacterial activities against gram-positive and gram-negative bacteria, viz., Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus, and Providencia rettegeri. Compounds 4c, 4d, 4f, 4g, and 4h showed their good activities against tested bacterial species. Pyrimidine derivatives 4d, 4f, and 4g have shown good antifungal activities against tested fungal strains, such as Aspergillus niger, Aspergillus fumigates, Aspergillus flavus, etc.

One-Pot Preparation of N,N'-Alkylidene Bisamide Derivatives Catalyzed by Silica Supported Magnesium Chloride (SiO2-MgCl2)

A highly efficient and simple procedure for the preparation of N,N'-alkylidene bisamides via one-pot threecomponent condensation reaction of phenyl acetylene/1-Hexyne, aromatic aldehyde and benzamide/acetamide in the presence of catalytic amount of silica supported magnesium chloride (SiO2-MgCl2) under thermal solvent-free conditions is described. All of the reactions proceeded in high yields and in relatively short reaction times. Keywords: Amide, Heterogeneous catalyst, N, N'-alkylidene bisamide, Silica Supported Magnesium Chloride (SiO2-MgCl2), aldehydes, alkyne, purification, pharmacological, oxazine, bisamides