One-pot Three-component Coupling Reaction Research Articles

1,2,4-Triazolo-quinazolinones as Effective Antifoulants: Molecular Design, Synthesis, and Biological Evaluation.

A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1-S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: Chlorella sp. and Chaetoceros curvisetus. The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1-S12 against both marine Gram-positive (Staphylococcus aureus) and Gram-negative (Vibrio parahemolyticus and Vibrio vulnificus) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[d]isothiazolyl butanoate (S10), benzo[d]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[d]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities.

One-Pot and Three-Component Coupling Synthesis of Novel p-[(Benzothiazolylamino)(aryl/heteroaryl)methyl]phenols and Its Corresponding O-Tosylates under Catalyst- and Solvent-Free Conditions

AbstractA catalyst- and solvent-free procedure has been developed for the synthesis of p-[( benzothiazolylamino)(aryl/heteroaryl)methyl]-functionalized phenols and its O-tosylates via one-pot three-component coupling reaction of thymol or carvacrol, aryl/heteroaryl aldehydes, and 2-aminobenzothiazoles with high selectivity. The present amino methylation process is convenient to perform even on large scale with a broad scope. The products were likely formed through the initial para attack of thymol on aldehydes to generate p-quinone methide intermediate and subsequent 1,6-aza-Michael addition of 2-aminobenzothiazoles on in-situ generated p-quinone methide intermediate.

An Interesting and Highly Efficient Route to 2-(Arylethynyl)Selanyl-Azoles: Fe3O4-Serine-CuI Nanocomposite Catalyzed Three-Component Coupling Reaction of Azoles, Se Powder, and Alkynes

2-(arylethynyl)selanyl-azoles are important and vital compounds that both azoles and aryl ethynyl selenides presented in their structure. In this article, we have constructed copper (I) iodide supported on the surface of magnetic Fe3O4 nanoparticles functionalized with Serine [Fe3O4-Serine-CuI] and evaluated its catalytic behavior in the preparation of 2-(arylethynyl)selanyl-azoles though one-pot three-component coupling reaction of azoles, Se powder and alkynes under ecofriendly conditions. The structure of Fe3O4-Serine-CuI nanocatalyst is well analyzed by several spectroscopic techniques like: FT-IR, SEM, EDX, TEM, MAP, XRD, TGA, VSM, ICP-OES techniques. High reusability and well characterization of Fe3O4-Serine-CuI nanocatalyst, high purity and yields of products, ecofriendly conditions, and simple operation are several considerable advantages this catalytic system.

Synthesis of 1-Aminoisoquinolines and Their Application in a Host-Guest Doped Strategy To Construct Ultralong Room-Temperature Phosphorescence Materials for Bioimaging.

Organic ultralong room-temperature phosphorescence (RTP) materials have attracted great attention for their wide applications in optoelectronic devices and bioimaging. However, the development of these materials remains a challenging task, partially due to the lack of rational molecular design strategies and unclear luminescence mechanisms. Herein, we present a method for facile access to structurally diverse substituted 1-aminoisoquinoline derivatives through a copper-catalyzed one-pot three-component coupling reaction that provides a promising approach to rapidly assemble a library of 1-aminoisoquinolines for exploring the regularity of the host-guest doped system. A series of host-guest RTP materials with wide-ranging lifetimes from 4.4 to 299.3 ms were constructed by doping various substituted isoquinolines derivatives into benzophenone (BP). Furthermore, 4 r/BP nanoparticles could be used for in-vivo imaging with a signal-to-noise ratio value as high as 32, revealing the potential of the isoquinoline framework for the construction of high-performance RTP materials.

A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies.

A dual catalytic system for cross-electrophile coupling reactions between aryl halides and alkyl halides that features a Ni catalyst, a Co cocatalyst, and a mild homogeneous reductant is described. Mechanistic studies indicate that the Ni catalyst activates the aryl halide, while the Co cocatalyst activates the alkyl halide. This allows the system to be rationally optimized for a variety of substrate classes by simply modifying the loadings of the Ni and Co catalysts based on the reaction product profile. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, and benzyl chlorides is demonstrated using the same Ni and Co catalysts under similar reaction conditions but with different optimal catalyst loadings in each case. Our system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-ortho-substituted aryl halides, pharmaceutically relevant druglike aryl halides, and a diverse range of alkyl halides. Additionally, the dual catalytic platform facilitates a series of selective one-pot three-component cross-electrophile coupling reactions of bromo(iodo)arenes with two distinct alkyl halides. This demonstrates the unique level of control that the platform provides and enables the rapid generation of molecular complexity. The system can be readily utilized for a wide range of applications as all reaction components are commercially available, the reaction is scalable, and toxic amide-based solvents are not required. It is anticipated that this strategy, as well as the underlying mechanistic framework, will be generalizable to other cross-electrophile coupling reactions.

Potassium salt promoted regioselective three-component coupling synthesis of 1,4-asymmetrical [60]fullerene bisadducts with superior electron transport properties.

An efficient one-pot three-component domino coupling reaction of phenols, C60, and bromoalkanes was developed, resulting in the highly regioselective synthesis of 1,4-asymmetrical C60 bisadducts. The reaction utilizes KOtBu as a promoter and likely proceeds by an oxyanion/carbanion rearrangement/nucleophilic addition cascade. This new methodology is particularly effective for the synthesis of 1,4-asymmetrical C60 electron transport materials. Its utility is demonstrated by the synthesis of a new efficient 1,4-C60 ETM, which possesses better performance, easier synthesis, and a lower cost compared with the commercially available PCBM.

Preparation of Ag2S Nanoparticles and using as Catalyst for the A3-coupling (Aldehyde-Amine-Alkyne) Reaction

Microwave assisted facile one-step approach was adopted to prepare mono-dispersed silver sulfide nanoparticles. The structures of the synthesized Ag2S nanoparticles were confirmed by Fourier-transform infrared spectroscopy (FT-IR), diffuse reflectance UV-vis spectroscopy (DRS), X-ray diffractometer (XRD), energy dispersive X-ray analysis (EDX) and transmission electron microscope (TEM). The prepared Ag2S nanoparticles (NPs) were successfully used as a heterogeneous catalyst in the one-pot three-component coupling reaction of aldehydes, amines and alkynes (A3-coupling) toward propargylamines. In this protocol, both aromatic and aliphatic aldehydes and secondary amines were reacted with terminal alkynes in the presence of Ag2S NPs at low catalytic loading (0.5 mol %) that led to the rapid and efficient formation of propargylamines with good to excellent yields. The A3-coupling reaction occurred effectively at 80 oC under solvent-free conditions. The catalyst is easy to prepare and is perfectly stable under the reaction conditions. Also, the Ag2S NPs catalyst can be easily recovered and reused several times and exhibited higher catalytic activity than other some commercially catalysts.

Three-component synthesis of amidomethylarenes and -heteroarenes over Hβ zeolite under solvent-free conditions

A highly efficient and eco-friendly protocol has been described for the synthesis of amidomethylarenes and -heteroarenes via one-pot three-component coupling reaction of amides, aldehydes and (hetero)arenes over a heterogeneous catalyst (Hβ zeolite) in solvent-free conditions. The scope and limitations of this catalytic process are demonstrated with various amides and arenes and the corresponding amidoalkylated arene products were obtained in moderate to excellent yields. The preliminary mechanistic insight (control experiments) suggest that bisamide and/or N-(hydroxymethyl)benzamide are probable intermediates in this reaction. Moreover, the catalyst can be reused without any significant loss of the catalytic activity and only water is produced as by-product.

Green synthesis and characterization of silver nanoparticles (Ag NPs) from extract of plant Radix Puerariae: An efficient and recyclable catalyst for the construction of pyrimido[1,2-b]indazole derivatives under solvent-free conditions

We have developed a green and environmentally friendly approach for the synthesis of silver nanoparticles (Ag NPs) using Radix Puerariae plant extract via a novel chemical route. The prepared Ag NPs has been characterized by TEM, XRD, SEM, DLS, EDX, and UV–Vis. Further, catalytic application of this fascinating nanomaterial has been utilized in the synthesis of biologically important pyrimido[1,2-b]indazole derivatives via one-pot three-component coupling reaction between aldehydes, alkynes and amines with excellent yields under solvent-free conditions. After completion of the catalytic reaction, the Ag NPs could be easily recovered and reused for four times without significant loss in its catalytic activity.

Nano ZrP2O7 Catalyzed Multicomponent Reaction for an Easy Access of 4H-pyrans and 1,4-dihydropyridines

ZrP2O7 nanoparticle catalyzed one-pot synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and ethyl acetoacetate. Also the synthesis of 1,4-dihydropyridines was investigated by using aldehydes, ethyl acetoacetate and ammonium acetate as utilizing nano structured ZrP2O7 as an efficient catalyst in ethanol. The attractive features of this process are mild reaction conditions, reusability of the catalyst, short reaction times, easy isolation of the products, and excellent yields.

L-Cysteine-functionalized magnetic nanoparticles (LCMNP): as a magnetic reusable organocatalyst for one-pot synthesis of 9-(1H-indol-3-yl) xanthen-4-(9H)-ones

l-Cysteine-functionalized magnetic nanoparticles (LCMNP) were introduced as an efficient and magnetically separable organocatalyst for the synthesis of 9-(1H-indol-3-yl) xanthen-4-(9H)-one derivatives. This class of compounds was synthesized via a one-pot three-component coupling reaction of 2-hydroxybenzaldehyde, dimedone, and indole in the presence of catalytic amount of LCMNP under mild and green conditions. High yields, short reaction time, easy workup, using environmental friendly conditions, and magnetic reusable catalyst are the advantages of this synthetic methodology. The LCMNP catalyst was reusable in this reaction at least for 6 times without significant decreasing in its catalytic activity.

Rapid Synthesis of D-A'-π-A Dyes through a One-Pot Three-Component Suzuki-Miyaura Coupling and an Evaluation of their Photovoltaic Properties for Use in Dye-Sensitized Solar Cells.

Twenty-four D-A'-π-A dyes were rapidly synthesized through a one-pot three-component Suzuki-Miyaura coupling reaction, which was assisted by microwave irradiation. We measured the absorption spectra, electrochemical properties, and solar-cell performance of all the synthesized dyes. The D5 πA4 dye contained our originally designed rigid and nonplanar donor and exerted the highest efficiency at 5.4 %. The short-circuit current (Jsc ) was the most important parameter for the conversion efficiency (η) in the case of the organic D-A'-π-A dyes. Optimal ranges for the D-A'-π-A dyes were observed for high values of Jsc /λmax at λ=560-620 nm, an optical-absorption edge of λ=690-790 nm, and EHOMO and ELUMO values of <1.14 and -0.56 to -0.76 V, respectively.

ChemInform Abstract: One‐Pot Solvent Free Synthesis of Some tert‐Indolylmethane Amine Derivatives by Fe(HSO4)3 as a Recyclable Catalyst.

Solvent-free synthesis of 3-substituted indole derivatives by a one-pot three-component coupling reaction between aldehyde, N-alkyl aniline and indole by Fe(HSO4)3 catalyzed is described. The noticeable features of this protocol are the simplicity of the procedure, easy synthesized, recyclable and inexpensive catalyst, no organic solvent and high yields in relatively short reaction times.

Supported nano gold catalyzed three-component coupling reactions of amines, dichloromethane and terminal alkynes (AHA)

A simple and efficient method for the synthesis of pharmaceutically relevant propargylamines through one-pot three-component coupling reactions of amines, CH2Cl2, and terminal alkynes (AHA) using nano Au/CeO2 as a heterogeneous catalyst is reported. The catalyst is characterized by DRX, DR-UV visible spectroscopy, and TEM. Gold particles are regularly distributed on ceria and range in size from 2 to 4nm.

A triazine-based porous organic polymer: a novel heterogeneous basic organocatalyst for facile one-pot synthesis of 2-amino-4H-chromenes

A new triazine-based porous organic polymer has been synthesized through the polycondensation of cyanuric chloride and tris(2-aminoethyl)amine and it is employed as a basic organocatalyst for one-pot three-component coupling reaction.

Green synthesis of 2-amino-7-hydroxy-4-aryl-4$H$-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl$_{2}$

A highly efficient and environmentally benign protocol for the synthesis of 2-amino-7-hydroxy-4-aryl-4$H$-chromene-3-carbonitrile derivatives in good to high yields (77%-97%) by one-pot three-component coupling reaction of aromatic aldehydes, malononitrile, and resorcinol under reflux condition was developed in aqueous media using ZnO nanoparticles that were prepared in the presence of mulberry leaf extract under mild conditions.

Carboxylic acid-grafted mesoporous material and its high catalytic activity in one-pot three-component coupling reaction

A new carboxylic acid functionalized mesoporous organic polymer has been synthesized via in situ radical polymerization of divinylbenzene and acrylic acid using a mesoporous silica as a seed during the polymerization process under solvothermal conditions. The mesoporous material MPDVAA-1 has been thoroughly characterized employing powder XRD, solid state 13C cross polarization magic angle spinning-nuclear magnetic resonance, FT-IR spectroscopy, N2 sorption, HR-TEM, and NH3 temperature programmed desorption-thermal conductivity detector (TPD-TCD) analysis to understand its porosity, chemical environment, bonding, and surface properties. The mesoporous polymer was used as a catalyst for a three comp onent Biginelli condensation between various aldehydes, β-keto esters, and urea/thioureas to give 3,4-dihydropyrimidine-2(1H)-ones. The reactions were carried out under conventional heating as well as solvent-free microwave irradiation of solid components, and in both the cases, the mesoporous polymer MPDVAA-1 proved to be a powerful, robust, and reusable catalyst with high catalytic efficiency.

One‐pot Solvent Free Synthesis of Some Tert‐indolylmethane Amine Derivatives by Fe(HSO4)3 as a Recyclable Catalyst

AbstractSolvent‐free synthesis of 3‐substituted indole derivatives by a one‐pot three‐component coupling reaction between aldehyde, N‐alkyl aniline and indole by Fe(HSO4)3 catalyzed is described. The noticeable features of this protocol are the simplicity of the procedure, easy synthesized, recyclable and inexpensive catalyst, no organic solvent and high yields in relatively short reaction times.

Synthesis of silver–graphene nanocomposite and its catalytic application for the one-pot three-component coupling reaction and one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles in water

A graphene based composite with silver nanoparticles has been synthesized via a simple chemical route and its catalytic activity has been tested for multi-component reactions and click reaction in a one-pot approach. This silver–graphene nanocomposite shows excellent catalytic activity at room temperature for three-component couplings between aldehydes, alkynes and amines (A3-coupling) and one-pot synthesis of 1,4-disubstituted 1,2,3-triazole via click reaction between in situ generated azides (derived from anilines or amines) and terminal acetylenes. This solid silver–graphene catalyst has been characterized by TEM, Raman, XRD and UV-Visible absorption spectra. The developed catalyst is air-stable, inexpensive, easy to prepare and can be facilely recovered and reused five times without significant decrease in activity and selectivity.

Nano copper(i) oxide–zinc oxide catalyzed coupling of aldehydes or ketones, secondary amines, and terminal alkynes in solvent-free conditions

A simple, efficient, and environmentally benign method has been described for the synthesis of propargylamines through a one-pot three-component coupling reaction of terminal alkynes, aldehydes or ketones, and secondary amines in excellent isolated yields, under solvent-free conditions, using a catalytic amount of nano Cu2O–ZnO as the recyclable, and heterogeneous catalyst. The catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for ten successive runs. The catalyst was characterized by using powder X-ray diffraction (XRD), a transmission electron microscopy (TEM), a scanning electron microscopy (SEM), BET surface area measurement and FT-IR spectroscopy.