Three-component Condensation Reaction Research Articles

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde.

The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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.

A facile one-pot ultrasound-assisted green synthesis of tetrahydrobenzo[b]pyrans catalyzed by gold nanoparticles supported on thiol-functionalized reduced graphene oxide

A convenient one-pot protocol was explored for the preparation of tetrahydrobenzo[b]pyrans. This reaction was carried out through a three-component condensation reaction of malononitrile, dimedone and aldehyde in the presence of gold nanoparticles on thiol-functionalized reduced graphene oxide as a catalyst in water under ultrasound irradiation. The pure products were obtained in high yields and short reaction times. Also, this catalyst can be easily separated from the reaction and recycled six times without activity loss.

A novel catalytic one-pot three-component reaction of aldehydes, o-phenylenediamine derivatives and isocyanides for synthesis of 3,4-dihydroquinoxalin-2-amine derivatives in the presence of zirconium tetrachloride

A simple and efficient one-pot procedure for the synthesis of biologically interesting 3,4-dihydroquinoxalin-2-amine derivatives through a three-component condensation reaction of o-phenylenediamines, carbonyl compounds and isocyanides in ethanol at room temperature is described. In this work, unlike the other methods, aldehydes reacted as well as ketones in the presence of 10 mol% of zirconium tetrachloride as catalyst to afford good to excellent yields of products. This methodology is of great value because of its environmentally benign character, high yields, ease of handling and reliable for both aldehydes and ketones. The newly synthesized compounds were systematically characterized by IR, 1H NMR, 13C NMR and elemental analysis. A novel catalytic one-pot three-component reaction of aldehydes, o-phenylenediamine derivatives and isocyanides for synthesis of 3,4-dihydroquinoxalin-2-amine derivatives in the presence of zirconium tetrachloride .

A novel copper complex supported on magnetic reduced graphene oxide: an efficient and green nanocatalyst for the synthesis of 1-amidoalkyl-2-naphthol derivatives

A new Cu(II) complex supported on magnetic reduced graphene oxide was prepared and characterized by various techniques, such as FT-IR, XRD, SEM, EDX, TEM, TGA, BET, ICP, and VSM. The synthesized nanocomposite, which has size distribution of 25–30 nm, was employed as catalyst in one-pot synthesis of 1-amidoalkyl-2-naphthols via three-component condensation reaction of amides, aromatic aldehydes, and 2-naphthol, under solvent-free conditions. The introduced catalysis procedure for the synthesis of 1-amidoalkyl-2-naphthol derivatives offers several advantages namely, short reaction times, high yields, facile recyclability, and cost effectiveness.

Microwave assisted synthesis and Anti-microbial activity of new Diethyl ((dialkoxyphosphoryl) (2-hydroxyphenyl) methyl) phosphoramidates

ABSTRACTThe synthesis of new α-aminophosphonates 4a-j (diethyl((dialkoxyphosphoryl)(phenyl)methyl)phosphoramidates) were achieved through a one pot simple and efficient method from the three-component condensation reaction (Kabachnik-Fields reaction) of diethyl phosphoramidate, aryl salicylaldehydes, and dialkyl phosphite by using microwave irradiation under solvent-free and catalyst-free conditions in good to excellent yields and short reaction times. The structures of the novel products were established by IR, 1H, 13C & 31P-NMR and Mass spectroscopy. All the synthesized compounds were screened their antimicrobial activity.

Synthesis and the antimicrobial activity of hexamethylene-Nmaleinimidospiroindole- 3,3’-pyrrolo[3,4-c]pyrrole derivatives

Aim. To synthesize a series of hexamethylene-N-maleinimidospiroindole-3,3’-pyrrolo[3,4-c]pyrrole derivatives, study the antimicrobial activity of the compounds synthesized and compare their antimicrobial activity with the antimicrobial activity of the bis-analogs previously synthesized. Materials and methods. The methods of organic synthesis, instrumental methods for determination of the molecular structure of organic compounds, agar well diffusion method were used. Experimental part. The interaction of isatins with a-amino acids and 1,6-bismaleinimidohexane in the equimolar ratio led to formation of 1′-(hexamethylene-N-maleinimido)-2a′,5a′-dihydro-1′H-spiroindol-3,3′-pyrrolo[3,4-c] pyrrol-2,2′,6′(1H,3′H,5′H)-trion derivatives. The structure of the compounds synthesized was reliably proven by the instrumental methods. Data of the microbiological screening showed a high level of the antimicrobial activity against Staphylococcus aureus and Candida albicans fungi. Conclusions. It has been determined that the three-component condensation reaction of isatins with α-amino acids and 1,6-bismaleinimidohexane in the equimolar ratio is an efficient synthetic method of 1′-(hexamethylene-N-maleinimido)-2a′,5a′-dihydro-1′H-spiroindol-3,3′-pyrrolo[3,4-c]pyrrol-2,2′,6′(1H,3′H,5′H)-trion derivatives, which reveal a high level of the antimicrobial activity against Staphylococcus aureus and Candida albicans fungi. 1’-(Hexamethylene-N-maleiimido)-5’-methyl-2a’,5a’-dihydro-1’H-spiroindol-3,3’-pyrrolo[3,4-c]pyrrol-2,2’,6’(1H,3’H,5’H)-trione has shown the highest antimicrobial activity among derivatives of hexamethylene-Nmaleinimidospiroindol- 3,3’-pyrrolo[3,4-c]pyrrols.

A Simple and Efficient Supramolecular Chemistry Approach for Synthesis of Bis(indolyl)methanes Using Aqueous β-Cyclodextrin as Green Promoter Host

Background: In the recent years, various bis-heterocyclic compounds are reported for their varied biological activities. Bis(indolyl)methanes and its derivatives are commonly present in over 3000 natural isolates and reported for its broad spectrum of biological activities. Though, there are so many methods reported for the synthesis of bis(indolyl)methanes, there is a need to develop a green and ecofriendly synthetic protocol which in turn is important for economic and synthetic point of view. Method: The supramolecular chemistry approach was efficiently used for the synthesis of bis(indolyl)methane derivatives 3(a-o) by the condensation reaction of indole 1 (2.0 mmol) and substituted aldehydes 2(a-o) (1.0 mmol) at 60°C using β-cyclodextrin in water. The progress of the reaction was monitored by TLC using ethyl acetate:hexane (7:3) as a mobile phase. The identity and purity of the products were confirmed by MASS, 1H NMR, and 13C NMR. Results: This report describes supramolecular synthesis of bis(indolyl)methanes 3(a-o) using β-cyclodextrin (1.0 mol%) in water at 60°C. The synthesized compounds 3(a–o) were obtained in excellent yields (80-92 %) in less reaction time (20-40 min). The hydrophobic binding of β-cyclodextrin with one of the reactants is explained by 1H NMR. The rate of the reaction is accelerated if electron withdrawing groups like Cl and F are present on the aromatic ring. Conclusion: We have efficiently synthesized bis(indolyl)methanes 3(a–o) via three-component one-pot condensation reaction of indole with substituted aldehydes using β-cyclodextrin as a supramolecular catalyst in aqueous medium. β-cyclodextrin is biodegradable, recoverable and purely environmentally benign. This method has several advantages over existing catalytic protocols as it has simple and green experimental procedures, use of green reaction media (water), lower reaction time, high reaction rate and avoids cumbersome work-up. Keywords: Supramolecular chemistry, β-cyclodextrin, water, bis(indolyl)methanes, one-pot reaction, green promoter.

An In Situ Procedure; Grinding Synthesis of 4H-benzo[h]chromene-3- carbonitriles Using DBU-hydrobromide-perbromide

Background: A clean and environmentally benign route to 4H-benzo[h]chromene-3- carbonitriles has been developed via three-component condensation reaction of various benzyl alcohols, malononitrile and 1-naphthol using DBU-hydrobromide-perbromide as an efficient oxidizing reagent at room temperature. Methodology: The present methodology offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions and reduced environmental consequences. Conclusion: All of synthesized compounds were characterized by IR, NMR and elemental analyses. Keywords: Chromene, benzyl alcohol, multicomponent reaction, 1-Naphthol, malononitrile, TFE.

Synthesis of Functionalized γ-Spiroiminolactones through a One-Pot Three-Component Reaction of Isocyanides, Acetylenic Esters, and 6H-Indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one

ABSTRACTA new and efficient isocyanide-based one-pot multi-component reaction has been described for the synthesis of novel ?-spiroiminolactone derivatives. Products were obtained by a three-component condensation reaction between isocyanides with acetylenic esters which was trapped with 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one (aromatic ketone) in CH2Cl2 without use of any catalyst or activator in excellent yields.

Synthesis of novel hydroxyspiro[indoline-3,9′-xanthene]trione derivatives using solid acids as catalyst

An eco-friendly method for the synthesis of hydroxyspiro[indoline-3,9′-xanthene]triones as new spiro[indoline-3,9′-xanthene]trione derivatives is described. These syntheses were accomplished via pseudo three-component condensation reaction of dimedone and isatin derivatives in the presence of silica-bonded n-propyltriethylenetetraminesulfamic acid in refluxing ethanol. Most of the acid catalysts gave spiro[indoline-3,9′-xanthene]triones as the final products. In the present method by using different amounts of acid catalyst and controlling the conditions, hydroxyspiro[indoline-3,9′-xanthene]triones were obtained as the only product. The advantages of our method are practical simplicity, using reusable heterogeneous catalyst, short reaction times, and good yields of the products. The recycled catalyst could be reused fifth times without appreciable loss in the catalytic activity. Two compounds were found to display in vitro antioxidant and cholinesterase inhibitory activities.

A Facile and Diastereoselective access to Functionalised Benzopyrano[3,4-a] Quinolizinesviaa Pyridine-Based Three-Component Reaction

The reaction of 2-oxo-2 H-chromene-3-carbonitriles with dialkyl acetylenedicarboxylates and pyridines results in a three-component condensation reaction in which the 2-oxo-2 H-chromene-3-carbonitrile group acts as a dipolarophile to produce benzopyrano[3,4- a] quinolizines under mild conditions in good yield.

One-pot Synthesis of Benzo[c]acridine Derivatives Using SBA-Pr-SO3H as Nano Catalyst

One-pot synthesis of benzo[c]acridine derivatives via the three-component condensation reaction of aromatic aldehydes, 1-naphtylamine, and dimedone using sulfonic acid functionalized SBA-15 (SBA-Pr-SO3H) as nanoporous acid catalyst under solvent-free conditions was studied. This reaction is an efficient, green and environmentally friendly procedure.

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.

An efficient domino one-pot synthesis of novel spirofuran-indenoquinoxalines by vinyltriphenylphosphonium salts

A simple and convenient multi-component domino reaction has been described for the synthesis of novel spirofuran-indenoquinoxaline derivatives. Products were obtained by a three-component condensation reaction between ninhydrin, aromatic 1,2-diamines and dialkyl ethynedicarboxylates in the presence of a catalytic amount of triphenylphosphine in $$\hbox {CH}_{2}\hbox {Cl}_{2}$$ at ambient temperature in excellent yields. This one-pot process produces biologically and pharmacologically significant heterocycles with the formation of five new bonds (one C–C, two C=N and two C–O) and two new rings in a single operation.

Convenient one-pot synthesis of thiobarbituro-quinoline derivatives via catalyst-free multicomponent reactions in water

A one-pot, three-component condensation reaction of 8-quinolinol, 2-thiobarbituric acid and isatins or aldehydes in water to give novel barbituroquinoline derivatives for the first time, is described. The reaction is free of catalysts and toxic solvents, operating under mild conditions and allows for ease of product isolation, making it more environmentally friendly and suitable for large-scale operations.