One-pot Three-component Condensation Reaction Research Articles

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

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.

One pot synthesis of aminonaphthoquinone derivatives using Cu(II) immobilized on hyperbranched polyglycerol functionalized graphene oxide as a reusable catalyst under solvent-free conditions

A new Cu(II) immobilized on hyperbranched polyglycerol (HPG) functionalized graphene oxide catalyst was prepared and characterized by FT-IR, TGA, FE-SEM, XRD, and ICP-OES techniques. This catalyst was used efficiently for the preparation of aminonaphthoquinones via one-pot three-component condensation reaction under solvent-free conditions. The catalyst could be easily recovered and reusable several times without a significant loss of activity, which make this method attractive and in a close agreement with green chemistry.

A novel sulfamic acid functionalized nano-catalyst on the basis of calix[4]resorcinarene for the green one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones under thermal solvent-free conditions

N-propyl sulfamic acid supported nano-catalyst on the basis of calix[4]resorcinarene was prepared via the efficient and facile reaction of amine functionalized polycalix[4]resorcinarene with chlorosulfonic acid. The achieved catalytic system was characterized using some spectroscopic techniques such as Fourier transform Infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), and CHNS elemental analysis. This newly developed acidic catalyst was employed efficiently in a one-pot three-component condensation reaction of aromatic aldehydes, dimedone and phthalhydrazide for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives through an easy and eco-friendly methodology. The catalyst was easily separated from the reaction mixture by simple filtration and the desired products were achieved in good to excellent yields in short reaction times.

SnO2 nanoparticles as an efficient heterogeneous catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones

A new protocol for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives is described via a one-pot three-component condensation reaction of phthalhydrazide, dimedone or 1,3-cyclohexanedione and aromatic aldehydes catalyzed by SnO2 nanoparticles as a heterogeneous catalyst under solvent-free conditions. The SnO2 nanoparticles (NPs) were characterized by FT-IR, X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM) and energy dispersive X-ray analyzer (EDAX). The advantages of the protocol are the shorter reaction time, simple work-up procedure and reusable catalyst.Graphical

Microwave-assisted multicomponent reaction for the synthesis of 2-amino-4H-chromene derivatives using ilmenite (FeTiO3) as a magnetic catalyst under solvent-free conditions

A green and highly efficient method has been developed for the synthesis of 2-amino-4H-chromene derivatives in the presence of FeTiO3 as magnetic catalyst via one-pot three-component condensation reaction of aromatic aldehydes, malononitrile and α- or β-naphthol without solvent under microwave irradiation. Mild reaction conditions, short reaction times, simple work-up, use of an economically convenient catalyst, and excellent product yields are the advantageous features of this method. The catalyst can be easily recovered by a simple magnetic separation and can be recycled six times with no significant loss of catalytic activity.

Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

Leucine, a naturally occurring α-amino acid, has been found as an effective catalyst to effect the one-pot three-component condensation reaction between aromatic aldehydes, malononitrile and 5,5-dimethyl-1,3-cyclohexanedione (dimedone). Various 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives are conveniently prepared by these reactions in excellent yields. High yields, short reaction times, simple work-up, use of green and naturally occurring catalyst and solvent are the main merits of the present protocol.

Application of novel nanostructured dinitropyrazine molten salt catalyst for the synthesis of sulfanylpyridines via anomeric based oxidation

1,4-Dinitropyrazine-1,4-diium trinitromethanide {[1,4-pyrazine-NO2][C(NO2)3]2} as a novel nanostructured molten salt (NMS) catalyzed the synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridine derivatives via the one-pot three-component condensation reaction between several aromatic aldehyde, malononitrile and benzyl mercaptan at room temperature under solvent-free conditions. The synthesized NMS catalyst was fully characterized by FTIR, 1H NMR, 13CNMR, mass, thermal gravimetric, X-ray diffraction patterns, scanning electron microscopy and transmission electron microscopy analysis. The major advantages of described methodology are mildness, ease of separation, good yields and short reaction times. A rational mechanism was suggested for the final step of the 2-amino-3,5-dicarbonitrile-6-sulfanylpyridines synthesis. We think that the proposed mechanism has potential for entering into the graduate text book in the future.

Preparation and application of a magnetic organic-inorganic hybrid nanocatalyst for the synthesis of α-aminonitriles

This article is the first report of the catalytic application of copper ferrite-coated chitosan in organic reactions as a bio-nanocomposite. CuFe2O4/chitosan was used as a hybrid nanocatalyst for the multicomponent Strecker synthesis of α-aminonitriles by using aryl aldehydes, trimethylsilyl cyanide (TMSCN) and aromatic amines at room temperature in ethanol as a green solvent. The catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), field-emission scanning electron microscopy (FE-SEM) and energy-dispersive X-ray spectroscopy (EDX) analyses. The nanocatalyst was recovered and reused several times without significant loss of catalytic activity. The organic products were obtained easily without need for column chromatography in good-to-excellent yields. A facile and highly efficient synthesis of α-aminonitriles is reported via a one-pot threecomponent condensation reaction of aryl aldehydes, trimethylsilyl cyanide and aniline at room temperature in the presence of CuFe2O4/chitosan as a hybrid nanocatalyst in ethanol as a green solvent.

Bionanostructure-catalyzed one-pot three-component synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent-free conditions

In this work, chitosan/graphene oxide as a green bionanocomposite catalyst was synthesized and characterized by Fourier transform infrared spectroscopy (FT-IR) spectra, thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) analysis, atomic force microscopy (AFM) and scanning electron microscopy (SEM) images. Then, it was used as a nanocatalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives by a one-pot three-component condensation reaction of benzaldehyde, 1,3-ketoesters and urea in excellent yields and short reaction times under solvent-free conditions. The reaction work-up was simple and the catalyst could easily be separated from the reaction mixture and reused in subsequent reactions.

Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two novel nanostructured catalysts: applications in the synthesis of Biginelli-type, polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives

Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two nanostructured novel, green and heterogeneous catalysts were designed, synthesized and fully characterized by FT-IR, energy-dispersive X-ray spectroscopy, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy and thermal gravimetric analysis. Then their catalytic applications were studied in the Biginelli-type reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via one-pot three-component condensation reaction between several aldehydes, ethyl acetoacetate and urea or thiourea. To further study catalytic properties of NMSDSA and NMSMSA, they were used in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives under same reaction conditions. NMSDSA and NMSMSA have advantages such as cost-effectiveness, cleaner reaction profile, benign and heterogeneous characters, reusability of the catalysts and being in agreement with the green chemistry protocols. The described nanostructured catalysts have natural-based acids and potential for industrial production. Synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via Biginelli-type reaction, polyhydroquinolines and 2,3-dihydroquinazolin-4(1H)-ones using NMSDSA and NMSMSA as two novel nanostructured catalysts.

ChemInform Abstract: Design, Synthesis, Characterization and Catalytic Performance of a New Cellulose‐Based Magnetic Nanocomposite in the One‐Pot Three‐Component Synthesis of α‐Aminonitriles.

A sulfonated magnetic cellulose-based nanocomposite was prepared and characterized using scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction and Fourier transform infrared spectroscopy. Then, it was used as a green nanocatalyst for the synthesis of α-aminonitriles by a one-pot three-component condensation reaction of aldehydes or ketones, amines and trimethylsilylcyanide in ethanol at room temperature. The reaction procedure is simple, yields are very high, reaction time is very short and the catalyst can be easily separated from the reaction mixture and reused in subsequent reactions without significant loss of catalytic activity. Copyright © 2016 John Wiley & Sons, Ltd.

Mixed cobalt/nickel metal–organic framework, an efficient catalyst for one-pot synthesis of substituted imidazoles

In the present work, a three-dimensional bimetallic metal–organic framework, [CoNi(µ3-tp)2(µ2-pyz)2] (tp = terephthalic acid, pyz = pyrazine) was applied as a highly efficient and recoverable heterogeneous catalyst. The catalyzed reaction was the one-pot three-component condensation reaction between benzil or benzoin with various substituted aromatic aldehydes and ammonium acetate to synthesize the corresponding imidazoles in solvent-free conditions and high to quantitative yields. The catalyst can be recycled at least five times without significant loss in the catalytic activity. To the best of our knowledge, 2,4,5-trisubstituted 1H-imidazoles were not previously synthesized using MOFs as heterogeneous catalyst. The structure of previously reported cobalt/nickel MOF has been confirmed by various techniques, such as X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, field emission scanning electron microscopy, energy dispersive X-ray spectroscopy, and Brunauer–Emmett–Teller.

Applications of a novel nano magnetic catalyst in the synthesis of 1,8-dioxo-octahydroxanthene and dihydropyrano[2,3-c]pyrazole derivatives

Imidazole-based ionic liquid-stabilized on silica coated Fe3O4 magnetic nano particles [nano-Fe3O4@SiO2@(CH2)3-Imidazole-SO3H]Cl as a novel heterogeneous acidic catalyst was designed, synthesized and fully characterized by FT-IR, thermo gravimetric analysis (TGA), differential thermal analysis (DTA), energy-dispersive x-ray spectroscopy (EDX), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), Brunauer–Emmett–Teller (BET) and inductively coupled plasma (ICP) analysis. The nano-structured organo solid catalyst as a novel, mild and full-fledged catalyst was used for the cascade synthesis of 1,8-dioxo-octahydroxanthene derivatives by the condensation reaction between dimedone and various aldehydes at 80°C under solvent-free conditions. Similarly, dihydropyrano[2,3-c]pyrazole derivatives were synthesized by the one-pot three-component condensation reaction of aldehydes, malononitrile and 3-methyl-1-phenyl-2-pyrazoline-5-one under solvent-free conditions at room temperature. To the knowledge of our science, this is the main investigation on the synthesis of [nano-Fe3O4@SiO2@(CH2)3-Imidazole-SO3H]Cl as a worthy heterogeneous nano magnetic solid acid for acid catalyzed organic reactions.

Polystyrene-supported p-toluenesulfonic acid (PS/PTSA): as a highly active and reusable heterogeneous bronsted acid catalyst for the synthesis of novel 1H-indol-3-yl-4H-chromene-3-carbonitriles under neat conditions

An efficient and environmentally benign protocol for the synthesis of a new class of diversely functionalized novel 1H-indol-3-yl-4H-chromene-3-carbonitriles has been described through one-pot three-component condensation reaction of 3-(1H-indol-3-yl)-3-oxopropanenitrile, 5,5-dimethylcyclohexane-1,3-dione, and various aldehydes in the presence of polystyrene-supported p-toluenesulfonic acid (PS/PTSA) under solvent-free conditions. The present methodology offers several advantages such as short reaction time, simple operational procedure, avoid toxic solvent, high yield of product and endures the substrate diversity. The PS/PTSA catalyst is readily available in stable form which is fairly inexpensive and can be easily recovered from the reaction medium without appreciable changes for further reuse in the consecutive reaction cycles effectively.

A facile and green approach for the synthesis of spiro[naphthalene-2,5′-pyrimidine]-4-carbonitrile via a one-pot three-component condensation reaction using DBU as a catalyst

A series of novel spiro[naphthalene-2,5′-pyrimidine]-4-carbonitriles were synthesized using 1,3-dimethylbarbituric acid, aldehydes and cyclohexylidene malononitrile in presence of DBU. The structures were confirmed by spectral data and X-Ray crystallography.

Preparation of neutral ionic liquid [2-Eim] OAc with dual catalytic-solvent system roles for the synthesis of 2-amino-3-cyano-7-hydroxy-4-(aryl)-4H-chromene derivatives

A novel ionic liquid namely 2-ethyl imidazolium acetate, [2-Eim] OAc, was synthesized, and characterized by studying its FT-IR, 1H and 13C NMR, UV, thermal gravimetric analysis (TGA), differential thermal analysis (DTA) diagrams, and controlled its pH in aqueous media. The described ionic liquid was used as an efficient, homogeneous and reusable catalyst for the synthesis of a good range of 2-amino-4H-chromene derivatives by one-pot three-component condensation reaction of various aldehydes, malononitrile, and resorcinol under solvent-free conditions. Also, optimization of the reaction conditions was investigated using the response surface methodology (RSM), (Central Composite Design (CCD)). Further, the catalyst could be reused and recovered at least four times without appreciable loss of activity.

ChemInform Abstract: Design of 1‐Methylimidazolium Tricyanomethanide as the First Nanostructured Molten Salt and Its Catalytic Application in the Condensation Reaction of Various Aromatic Aldehydes, Amides and β‐Naphthol Compared with Tin Dioxide Nanoparticles.

1-Methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a novel, green and nano molten salt catalyst was designed and fully identified by IR, 1H NMR, 13C NMR, mass, thermal gravimetric (TG), derivative thermal gravimetric (DTG), X-ray diffraction (XRD) pattern, scanning electron microscopy (SEM) and transmission electron microscopy (TEM) analyses. The catalytic application of {[HMIM]C(CN)3} for the one-pot three-component condensation reaction of various aromatic aldehydes, amides and β-naphthol was studied through the preparation of 1-amidoalkyl-2-naphthols at room temperature under solvent-free conditions in comparison with nano SnO2. In the presented investigations, some products were produced and reported for the first time.

Synthesis and characterization of new 1-(α-aminoalkyl)-2-naphthols using pyrazine-1,4-diium trinitromethanide {[1,4-DHPyrazine][C(NO2)3]2} as a novel nano-structured molten salt and catalyst in compared with Ag–TiO2 nano composite

Pyrazine-1,4-diium trinitromethanide {[1,4-DHPyrazine][C(NO2)3]2} as a green and novel nano-structured molten salt catalyzed the synthesis of new 1-(α-aminoalkyl)-2-naphthol derivatives via the one-pot three-component condensation reaction between 2 or 4-aminopyridine, aromatic aldehydes and β-naphthol at room temperature under solvent-free conditions in comparison with Ag–TiO2 nano composite. Some advantages of the offered method are excellent cost effectiveness, catalytic efficiency, recycle and reusability of the catalyst. Pyrazine-1,4-diium trinitromethanide {[1,4-DHPyrazine][C(NO2)3]2} was fully characterized by IR, 1H NMR, 13C NMR, mass, thermal gravimetry (TG), derivative thermal gravimetry (DTG), differential thermal (DTA), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) analysis.

Hydrated Ferric Sulfate [Fe2(SO4)3·xH2O]: An Efficient and Reusable Catalyst for One-Pot Synthesis of 2H-Indazolo[2,1-b]phthalazine-triones

Hydrated ferric sulfate can be used as an efficient and reusable catalyst for the synthesis of 2H-indazolo(2,1- b)phthalazine-trione derivatives via one-pot three-component condensation reaction of phthalhydrazide, aromatic aldehydes and cyclic-1,3-diketones in ethanol under reflux conditions.

Application of silica-bonded imidazolium-sulfonic acid chloride (SBISAC) as a heterogeneous nanocatalyst for the domino condensation of arylaldehydes with 2-naphthol and dimedone

In this work, a novel nanostructured silica-bonded ionic liquid namely silica-bonded imidazolium-sulfonic acid chloride (SBISAC) has been prepared, and characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), transmission electron microscopy (TEM) and energy dispersive X-ray analysis (EDX) spectra. Then, SBISAC was utilized as an efficient and heterogeneous nanocatalyst for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones via the one-pot three-component condensation reaction of arylaldehydes with 2-naphthol and dimedone (5,5-dimethylcyclohexane-1,3-dione) under solvent-free conditions.