Three-component Condensation Of Aromatic Aldehydes Research Articles

A Novel Efficient and Biodegradable Natural Catalyst and Bio Based Solvents for the Green One Pot Three Component Synthesis of Tetrahydrobenzo[B]pyran and 3,4-Dihydropyrano[C]chromenes

This study presents a novel and efficient method for synthesizing Tetrahydrobenzo[b]pyran and 3,4-Dihydropyrano[c]chromene derivatives using honey as a highly efficient homogeneous catalyst. Through a one-pot three-component condensation of aromatic aldehydes with malononitrile and dimedone or 4-hydroxycoumarin, excellent yields were achieved under environmentally friendly conditions. The utilization of honey, a non-toxic and biodegradable catalyst, underscores the method's significance in green chemistry. The abstract highlights the method's advantages, including high yields, short reaction times, simple work-up, and its potential for applications in the green pharmaceutical and chemical industries. Additionally, the intricate role of honey as a catalyst in chemical reactions is explored, shedding light on its mechanism and potential applications in organic synthesis and other chemical processes. This research introduces a promising and environmentally friendly approach for the green synthesis of biologically active heterocyclic compounds using a natural, biodegradable catalyst, contributing significantly to the advancement of green chemistry practices.

Synthesis and some properties of 2-amino-4-aryl-6-hexyl7-hydroxy-4<i>h</i>-chromene-3-carbonitriles

Three-component condensation of aromatic aldehydes with malononitrile and 4-hexylresorcinol in toluene in the presence of a base leads to the formation of 2-amino-4-aryl-6-hexyl-7-hydroxy-4 H -chromene-3-carbonitriles in good yields (79-90%). Structure of the compounds was studied using the methods of two-dimensional NMR spectroscopy. Bioavailability parameters were predicted in silico , and possible protein targets were predicted by protein-ligand docking.

Barium silicate nanoparticles, an efficient catalyst for one-pot green synthesis of α-benzyl amino coumarin derivatives as potential chemotherapeutic agents.

A new, simple, and efficient method for synthesis of α-benzyl amino coumarin and its derivatives (1-24) is described via a one-pot, three-component condensation of aromatic aldehydes, amine, and 4-hydroxycoumarin under green chemistry conditions: water as a solvent and BaSiO3 nanoparticles as catalyst. BaSiO3 nanoparticles and all synthesized derivatives were characterized by multiple methods including; XRD, NMR, and FE-SEM. This method which gives higher yields, is also less expensive, and more environmentally friendly compared with other methods in the literature. In silico physicochemical and pharmacokinetics analyses were done on all synthesized compounds and indicated that these α-benzyl amino coumarins would be effective scaffolds for the future development of chemotherapeutic agents.

Introduction of an Efficient Protocol for the Synthesis of Some of the Pyrimidine Derivatives under Solvent-Free Conditions

Various pyrimidine derivatives were synthesized via one-pot three-component condensation of aromatic aldehydes, malononitrile, and multiple amines using 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) hydroxide as a basic ionic liquid catalyst under solvent-free conditions. The advantages of this method are the simplicity of the procedure, short reaction times, high yields, no-column chromatographic separation, commercial availability of the preliminary materials, and reusability of the catalyst.

A facile and efficient synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives using phosphate fertilizers MAP, DAP, and TSP as heterogeneous catalysts

A simple and efficient one-pot synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives was described. These reactions were realized through a three-component condensation of aromatic aldehyde, malononitrile, and 5,5-dimethyl-1,3-cyclohexanedione or 4-hydroxy-6-methylpyran-2-one using phosphate fertilizers monoammonium phosphate, NH4(H2PO4)2, (MAP), diammonium phosphate, (NH4)2(HPO4), (DAP), and triple superphosphate, Ca(H2PO4)2.H2O, (TSP) as heterogeneous catalysts. Under optimal reaction conditions, these fertilizers show an excellent catalytic activity. Indeed, the tetrahydrobenzo[b]pyrans and dihydropyrano[4,3-b]pyrans derivatives were obtained with good yields in short reaction times. Also, these fertilizers can be reused at least four times without significant loss of their catalytic activity. Therefore, their application can be contributing to the development of green chemistry.

Nano-ZnO Impregnated on Starch—A Highly Efficient Heterogeneous Bio-Based Catalyst for One-Pot Synthesis of Pyranopyrimidinone and Xanthene Derivatives as Potential Antibacterial Agents

A new method has been proposed for the synthesis of pyranopyrimidinone and xanthene derivatives using zinc oxide–starch nanocomposite as catalyst under microwave irradiation. The ZnO–starch nanocomposite was characterized by X-ray diffraction and scanning electron microscopy data, and the size of the ZnO-starch nanocomposite particles was estimated at 70–90 nm. The catalyst was used in the three-component condensation of aromatic aldehydes with barbituric acid and malononitrile and the 1:2 condensation of aromatic aldehydes with naphthalen-2-ol to obtain pyranopyrimidinone and xanthene derivatives, respectively. The catalyst can be reused several times without loss of catalytic activity. The proposed procedure utilizes affordable and inexpensive materials, provides excellent yields in short reaction time, and is eco-friendly, which makes it more economic than conventional methods. The antibacterial activity of the synthesized compounds was evaluated against M. luteus and P. aeruginosa.

One-pot three-component synthesis of 1,8-dioxooctahydroxanthenes and 14-Aryl-14Hdibenzo[a,j]xanthenes using a new nanostructure zeolite

A new modified zeolite containing Fe nanoparticles loaded in zeolite X (Fe-X) has been synthesized and characterized by FT-IR, XRD, EDX and SEM techniques and its catalytic activity has been investigated in the synthesis of two series of xanthene derivatives. We have described an efficient and novel method using Fe-X as a new and reusable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes derivatives from one-pot three-component condensation of aromatic aldehyde and dimedone or β-naphthol under solvent-free conditions. The significant advantages of the present method are high yields of products, short reaction time, easy separation of the catalyst from the reaction mixture, easy product isolation, solvent-free condition and reusability of the catalyst. A new modified zeolite containing Fe nanoparticles loaded in zeolite X has been synthesized, characterized and applied in the synthesis of two series of xanthene derivatives.

Electrogenerated base-promoted synthesis of 4-aryl-5-benzoyl-2-hydroxy-6-(trifluoromethyl)-1,4-dihydropyridine-3-carbonitriles nanoparticles by three-component condensation of aromatic aldehydes, malononitrile and 4,4,4-trifluoro-1 -phenylbutane-1,3-dione

An electrochemical strategy to the synthesis of novel 4-aryl-5-benzoyl- 2-hydroxy-6-(trifluoromethyl)-1,4-dihydropyridine-3-carbonitriles nanoparticles via three-component reaction of aromatic aldehydes, malononitrile and 4,4,4-trifluoro-1-phenylbutane-1,3-dione in water/ethanol in an undivided cell in the presence of sodium bromide as an electrolyte is described. This method has several advantages, such as high to excellent product yields (65?85 %), atom economy, environment friendly, and no need for chromatographic separations.

NH3(CH2)5NH3BiCl5 as a new hybrid and efficient catalyst for the synthesis of 1-(benzothiazolylamino)methyl-2-naphthol derivatives under solvent-free conditions

Abstract A simple, efficient and green procedure for synthesis 1-(benzothiazolylamino)methyl-2-naphthol derivatives via one-pot three-component condensation of aromatic aldehydes, β-naphthol and 2-aminobenzothiazole has been studied by using a novel hybrid catalyst NH3(CH2)5NH3BiCl5 under solvent-free conditions at 100 °C. This method has several advantages such as operational simplicity, recyclability of catalyst, easy workup, short reaction time and excellent yields.

Synthesis of 9-Arylhexahydroacridine-1,8-diones Using Phosphate Fertilizers as Heterogeneous Catalysts

A new strategy has been proposed for the synthesis of 9-arylhexahydroacridine-1,8-diones by three-component condensation of aromatic aldehydes with 5,5-dimethylcyclohexane-1,3-dione and ammonium acetate in ethanol, using nontoxic, available, and inexpensive phosphate fertilizers [monoammonium phosphate (MAP), diammonium phosphate (DAP), and triple super phosphate (TSP)] as heterogeneous catalysts. Notable advantages of the proposed method include operational simplicity, low cost of the reactants, favorable environmental profile, good yield, short reaction time, recovery and reuse of the catalyst, and valorization of Moroccan natural phosphate.

Synthesis of Novel 2-Amino-7-Methyl-4-Aryl-3-(Phenylsulfonyl)Pyrano[4,3-b]Pyran-5(4H)-One Derivatives in the Presence TiCl4 Supported on Kaolin as a Nano Catalyst

Novel 2-amino-7-methyl-4-aryl-3-(phenylsulfonyl) pyrano[4,3-b]pyran-5(4H)-one derivatives containing both biologically active pyran and chromene templates are synthesized via one-pot three-component condensation of aromatic aldehydes, 4-hydroxy-6-methyl-2H-pyran-2-one and phenylsulfonylacetonitrile in the presence of nano kaolin/TiCl4 as an efficient and recyclable acid catalyst. Many instrumental techniques including TEM, FE-SEM, and EDX, confirmed the structure of applied nano kaolin supported titanium tetrachloride. The proposed approach has some advantages as excellent yields, mild reaction conditions, eco-friendly, ease of work-up, survival of different functional groups and short reaction times.

Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes

In this abstract, we discuss the progress related to sulfonated carbon-based materials in various acid-catalyzed organic transformations which are then further utilized in medicinal field, laboratories and industries. A simple and novel methodology was employed to prepare carbon-based nanocatalyst, i.e. cellulose[2-(sulfooxy)ethyl]mercaptosulfonic acid as a solid acid catalyst. This nanocatalyst is recyclable and also exhibited very high activity. Novel carbon-based nanocatalyst, i.e. cellulose[2-(sulfooxy)ethyl]mercaptosulfonic acid[SEMSA] was successfully synthesized by reacting mercaptoethanol and chlorosulfonic acid, and the catalytic activity of the prepared catalysts was evaluated for the one-pot synthesis of gem-bisamides from various aldehydes and benzamide, hexahydroacridine-1,8-diones via three-component condensation of aromatic aldehyde, dimedone and ammonium acetate or aromatic amine and 1,8-dioxo-octahydroxanthenes using aldehyde and dimedone. Application of this new heterogeneous nanocatalyst system offered the advantages of high yields, short reaction times, eco-friendly nature and easy work-up procedure compared to the conventional methods of the synthesis, and confirmation of products synthesized has been done using studies like 1H NMR and 13C NMR. Among the various catalysts, this nanocatalyst, i.e. cellulose [2-(sulfooxy)ethyl]mercaptosulfonic acid[SEMSA], was found to be the most active and selective and could be recycled several times without significant loss of activity. Also, scanning electron microscopy and transmission electron microscopy of the catalyst have been performed to know the internal and external morphology, size, thermo-gravimetric analysis to study the thermal stability and Fourier transform infrared spectroscopy to study the modification pattern of the catalyst have been undertaken and presented in this work. Due to its simple and inexpensive solid support, i.e. cellulose and environmentally benign toluene, ethanol and acetonitrile as solvents in three different transformations which are less toxic, easily available and less expensive than other solvents. We reported here a novel route for the synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes

Pentaerythritol as efficient H-bonding organocatalyst for synthesis of indazolo[2,1-b]phthalazine-trione derivatives

Pentaerythritol was applied as an effective, biodegradable, nontoxic, mild, and commercially available H-bonding organocatalyst for synthesis of indazolo[2,1-b]phthalazine-trione derivatives via one-pot three-component condensation of aromatic aldehydes, phthalhydrazide, and dimedone under thermal solvent-free conditions in high to excellent yield.

Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2: a novel and efficient nano-catalyst for the one-pot three-component synthesis of pyran annulated bis-heterocyclic scaffolds under ultrasound irradiation

In this study, a novel magnetically recoverable Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2 nano-particle was synthesized using a simple chemical coprecipitation approach. In the FT-IR spectroscopy of nano-particles, related absorption peaks appeared which confirmed the successful synthesis of nano-catalyst. In the EDX spectrum of the nano-catalyst, the expected elements on their regions appeared. The XRD diffusion patterns of nano-catalysts showed the crystalline dispersions of Fe3O4 magnetic nano-particles. According to the FE-SEM and TEM images, the nano-particles have relative mono-dispersity and the average size of nano-particles is around 35 nm. The catalytic activities of the novel magnetic nano-particle were evaluated in the one-pot three-component synthesis of a wide variety of pyran annulated bis-heterocyclic derivatives (38 compounds) under ultrasonic irradiation. A simple, facial and highly efficient ultrasound-assisted method has been introduced for the synthesis of fused bis-heterocyclic pyran derivatives by one-pot, three-component reactions at room temperature. A series of pyrano[3,2-c]chromene derivatives were synthesized using a novel nano-catalyst via the condensation reaction of different aldehydes, malononitrile and 4-hydroxycoumarin. Kojic acid was also used in the three-component reaction for the synthesis of pyrano[3,2-b]pyran derivatives. The method was successful in the synthesis of various pyrano[2,3-d]pyrimidine derivatives. Additionally, new ultrasound-assisted synthesis protocol was used for the synthesis of novel chromeno[2,3-d]pyrimidine derivatives via three-component condensation of aromatic aldehydes, orcinol and barbituric acid. The new catalytic method exhibits some notable advantages such as short reaction times, operational simplicity, green reaction conditions, high yields and easy work-up and purification steps. In addition, the novel magnetic nano-particle could be easily separated by an external magnet and reused for six times without significant loss of its catalytic activity in the reaction.

CERIUM (IV) AMMONIUM NITRATE (CAN) AS A CATALYST IN WATER: A SIMPLE, PROFICIENT AND GREEN APPROACH FOR THE SYNTHESIS OF TETRAHYDROPYRIMIDINE QUINOLONES

We report here a facile, mild and efficient synthesis of functionalized tetrahydropyrimidine quinolones via one pot three-component condensation of aromatic aldehydes, N,N-dimethyl barbituricacid (barbituricacid), 4-hydroxy-1-methylquinolin-2(1 H )-one and using a cerium ammonium nitrate (CAN) as a green catalyst in aqueous media-water (as a green ideal solvent) is described. The significant advantages of this protocol are short reaction time, simple work up procedure and reduced environmental impact, wide substrate scope; generally very good to excellent yields and starting materials are inexpensive and commercially available. The structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR spectra.

SBA-15/hydrotalcite nanocomposite as an efficient support for the immobilization of heteropolyacid: A triply-hybrid catalyst for the synthesis of 2-amino-4H-pyrans in water

To circumvent the high solubility and low surface area of heteropolyacid and in attempt to develop a bi-functional heterogeneous catalyst for promoting organic transformations, heteropolyacid was embedded in functionalized SBA-15 and subsequently hybridized with layered double hydroxide. The catalyst could be considered as a bi-functional catalyst with both acidic and basic properties. The acidic properties emerged from the SBA-15 and heteropolyacid component while layered double hydroxide render the catalyst basic. The catalyst was characterized by using SEM/EDX, FT-IR, XRD, ICP-AES, BET and elemental mapping analysis. The catalytic activity of the catalyst was studied for promoting one-pot three-component condensation of aromatic aldehydes, malononitrile or ethyl cyanoacetate and C-H activated acidic molecules in aqueous media for the synthesis of 2-amino-4H-pyran derivatives. The catalyst exhibited high catalytic activity, which was superior to the previously reported ones. Moreover, the reusability of the catalyst was excellent and the leaching of heteropolyacid was dramatically suppressed. High yields, short reaction times, eco-friendly conditions, simplicity of the procedure, reusability of the catalyst and broad substrate scope are the merits of this protocol.

Three-component synthesis of 5-aryl-1,8-naphthyridine-3-carbonitriles

A procedure has been developed for the synthesis of highly functionalized 1,8-naphthyridines by three-component condensation of aromatic aldehydes with malononitrile dimer and enamino ketones.

A green protocol for one-pot three-component synthesis of 1-(benzothiazolylamino) methyl-2-naphthol catalyzed by oxalic acid

One-pot, efficient three-component condensation of aromatic aldehydes, 2-naphthol and 2-aminobenzothiazole in the presence of oxalic acid as an organocatalyst and effective catalyst for the synthesis of 1-(benzothiazolylamino) methyl-2-naphthol derivatives under thermal and solvent-free conditions is described. The present approach of this methodology offers several advantages such as high yields, clean reaction profiles, operational simplicity, being environmentally benign, lack of need for column chromatography and simple work-up procedure.

An Improved Procedure for the Three-Component Synthesis of 1H-Pyrazolo[1,2-B]Phthalazine-5,10-Dione Derivatives Using Basic Ionic Liquid

An efficient and green method for the synthesis of 1 H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives has been achieved through the one-pot, three-component condensation of aromatic aldehydes, malononitrile or ethyl cyanoacetate, and phthalhydrazide in the presence of 1-butyl-3-methyl imidazolium hydroxide ([bmim]OH) as catalyst in EtOH. This reaction does not involve any hazardous organic solvent and toxic catalyst. The ionic liquid can be recovered and recycled for subsequent reactions. Moreover, this protocol has the advantages of easy work-up, short reaction time, mild reaction conditions and environmentally benign procedures compared with the reported methods.

Convenient and efficient method for synthesis of 2,4,6-triarylpyridines using catalytic amount of PEG1000-based dicationic acidic ionic liquid under solvent-free conditions

ABSTRACTA convenient and efficient method for synthesis of substituted 2,4,6-triarylpyridines by the reaction of chalcones and ammonium acetate or via one-pot, three-component condensation of aromatic aldehydes with acetophenones and ammonium acetate has been developed by using the efficient catalyst PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL) under solvent-free conditions. Recycling studies have shown that the PEG1000-DAIL can be readily recovered and reused several times without significant loss of activity.