One-pot Three-component Synthesis Research Articles

An Efficient and Rapid Synthesis of 1,4-Dihydropyrano[2,3-c]Pyran and 1,4-Dihydropyrano[2,3-c]Quinoline Derivatives Using Copper Nanoparticles Grafted on Carbon Microspheres

A rapid and efficient one-pot three-component synthesis of 2-amino-3-cyano-4-aryl-7-methyl-5-oxo-4,5-dihydro-pyrano-[3,2-c]pyran and 2-amino-3-cyano-4-aryl-6-methyl5,6-dihydro-5-oxo-4H-pyrano-[3,2-c]quinoline derivatives catalyzed by copper nanoparticles grafted on carbon microspheres is developed. The use of heterogeneous catalyst, mild reaction conditions, and excellent yield of the corresponding products are the key features of the present protocol.

One-Pot Three-Component Synthesis of 2-Amino-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile Derivatives Catalyzed by Cobalt Doped Iron (III) Tartrate Complex

An environmentally friendly one-pot three-component strategy synthesizing a series of 2-Amino-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives has been successfully performed in water. The products were obtained through conventional and microwave irradiation, which involving aldehyde, malononitrile, and 4-hydroxy coumarin, resulting in a green synthetic protocol with a high atom economy. The reaction was catalyzed by a water-soluble and reusable catalyst, i.e., cobalt doped iron (III) tartrate complex. The catalyst was recovered and efficiently reused.

Synthesis and Cytotoxic Activity of Novel Indole Derivatives and Their in silico Screening on Spike Glycoprotein of SARS-CoV-2.

This work investigated the interaction of indole with SARS-CoV-2. Indole is widely used as a medical material owing to its astounding biological activities. Indole and its derivatives belong to a significant category of heterocyclic compounds that have been used as a crucial component for several syntheses of medicine. A straightforward one-pot three-component synthesis of indole, coupled with Mannich base derivatives 1a–1j, was synthesized without a catalyst. The products were confirmed by IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analysis. The indole derivatives were tested for cytotoxic activity, using three cancer cell lines and normal cell lines of Human embryonic kidney cell (HEK293), liver cell (LO2), and lung cell (MRC5) by MTT assay using doxorubicin as the standard drug. The result of cytotoxicity indole compound 1c (HepG2, LC50−0.9 μm, MCF−7, LC50−0.55 μm, HeLa, LC50−0.50 μm) was found to have high activity compared with other compounds used for the same purpose. The synthesized derivatives have revealed their safety by exhibiting significantly less cytotoxicity against the normal cell line (HEK-293), (LO2), and (MRC5) with IC50 > 100 μg/ml. Besides, we report an in silico study with spike glycoprotein (SARS-CoV-2-S). The selective molecules of compound 1c exhibited the highest docking score −2.808 (kcal/mol) compared to other compounds. This research work was successful in synthesizing a few compounds with potential as anticancer agents. Furthermore, we have tried to emphasize the anticipated role of indole scaffolds in designing and discovering the much-awaited anti-SARS CoV-2 therapy by exploring the research articles depicting indole moieties as targeting SARS CoV-2 coronavirus.

Keggin-type heteropoly-11-molybdo-1-vanadophosphoric acid supported montmorillonite K-10 clay-catalysed one-pot multi-component synthesis of chromeno[2,3-b]indoles

One-pot three-component synthesis of twelve different chromeno[2,3-b]indole derivatives were achieved by the condensation of β-naphthol, oxindole and various substituted aldehydes. Two more chromeno[2,3-b]indole derivatives were also synthesized through one-pot two-component condensation of salicylaldehyde with oxindole/chlorooxindole. Both the condensations were achieved by using Keggin-type heteropoly-11-molybdo-1-vanadophosphoric acid, H4[PVMo11O40] supported on montmorillonite K-10 clay for about 10% as catalyst under environmentally benign solvent-free reaction condition. Shorter reaction time, excellent yield of product, sustainability of catalytic material and simple workup procedure under green experimental conditions are the advantages of this protocol.

One-pot three-component synthesis of a new series of tetrahydrobenzofuran-chromone conjugates

An efficient one-pot three-component protocol for the synthesis of novel tetrahydrobenzofuran-chromone conjugates using 3-formylchromones and 1,3-cyclohexandiones in the presence of a variety of alkyl or aryl isocyanides was developed. The reaction sequence consists of an initial Knoevenagel condensation of aromatic aldehydes with 1,3-cyclohexandione derivatives, followed by a [4 + 1] cycloaddition of with isocyanides, and then imine-enamine tautomerization to afford the products.

Organobase-catalyzed one-pot three-component synthesis of novel pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives

An efficient, simple and fast procedure has been developed for the synthesis of a novel types of pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives through the one-pot three-component condensation reaction of 7-hydroxy-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-one, malononitrile and aromatic aldehydes in the presence DIPEA (N,N-diisopropylethylamine) as an available organo-base catalyst. This proposed procedure leads to the synthesis of desired products in short reaction times (5–10 min) and excellent isolated yields (90–94%).

Three-component one-pot synthesis of new spiro[indoline-pyrrolidine] derivatives mediated by 1,3-dipolar reaction and DFT analysis

A suitable one-pot sequential three-component synthesis of a series of new spiro[indoline-pyrrolidine] derivatives is described. Reactions proceeded through a 1,3-dipolar cycloaddition between azomethine ylides, generated in situ from the condensation of isatins with sarcosine, and trans-1,2-dibenzoylethylene as dipolarophile under conventional heating. This protocol provides a mild reaction condition with operational simplicity, affording high regioselectivity and stereoselectivity, enabling to assemble a complex structural entity in a single step in good to excellent yields. The regio- and stereochemical outcome of this cycloaddition reaction was ascertained by spectroscopic analysis. Also, DFT quantum chemical calculation was used to establish the geometries and electronic structures of the obtained compounds.

Aerobic Oxidative C-H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin-Iodine-Coupled Organocatalysis.

The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.

Multicomponent synthesis, DFT calculations and molecular docking studies of novel thiazolyl-pyridazinones as potential antimicrobial agents against antibiotic-resistant bacteria

Novel series of aryl(hetaryl)thiazolylpyridazinedione derivatives were synthesized via one-pot three-component synthesis of maleic anhydride, thiosemicarbazide and the appropriate α-bromoketones using cellulose sulfuric acid (CSA) as an eco-friendly catalyst under microwave irradiation (MWI) in high, efficient yields and short reaction time and the achieved results showed the tremendous synergistic effect between CSA and MWI. All the prepared compounds were fully characterized by spectral methods (IR, Mass, 1H NMR and 13C NMR) and an alternate method. Moreover, in-vitro biological activities of the obtained candidate molecules as antibacterial and/or antifungal agents were investigated against S. aureus, MRSA and C. albicans, and the results were compared with those of standard compounds. The results showed that compound 19 has an excellent antibacterial (S. aureus, MIC: 0.12 μg/mL) and antifungal (C. albicans, MIC: 3.90 μg/mL) activities. In addition, compound 5c demonstrated the highest antibacterial activity against P. aeruginosa (MIC: 0.12 μg/mL). The molecular structures, reactivity and electronic properties of candidate compounds demonstrating the best promising antimicrobial activities were studied at the B3LYP/6–311 G level of theory and their quantum mechanical parameters were computed. The energy gaps of all of the selected compounds were found to range between 3.1 and 3.6 eV. Furthermore, molecular docking with the most common protein receptors of the microorganisms of interest (SAP2 and FabI) was performed.

Bicyclic [1,3,4]Thiadiazolo[3,2-α]Pyrimidine Analogues: Novel One-Pot Three-Component Synthesis, Antimicrobial, and Antioxidant Evaluation

A novel one-pot three-component synthesis of 1-(7-methyl-2,5-diphenyl-5H-[1,3,4]thiadiazolo(3,2-α)pyrimidine-6-yl)ethanone (4a-i) derivatives via cyclo-condensation of substituted 2-amino-[1,3,4]thiadiazole (1a-c), acetylacetone (2) and various aromatic aldehydes (3a-c) in the presence of p-toluene sulfonic acid (PTSA) in acetonitrile. Spectral data and elemental analysis have characterized the newly synthesized compounds. The new analogs were screened for their antibacterial and antifungal activities. The majority of the tested compounds displayed significant to moderate efficacy against most of the designated organisms. Among the tested compounds, 4b, 4e, and 4h showed noteworthy efficacy against selected microbes, and compounds 4c and 4i were found to be exceptionally efficient against selected fungal strains. Compound 4c, 4e, 4f, 4i were also designated as best antioxidants against NOx.

One-Pot Three-Component Synthesis of Novel 1,5-Benzodiazepine Derivatives and Theiranti-BVDV (Bovine Viral Diarrhea Virus) Activity

One-Pot Three-Component Synthesis of Novel 1,5-Benzodiazepine Derivatives and Their<i>anti</i>-BVDV (Bovine Viral Diarrhea Virus) Activity

Correction: One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight

Correction for ‘One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight’ by Vu Thanh Nguyen et al., New J. Chem., 2021, 45, 2053–2059, DOI: 10.1039/d0nj05687a.

Zr@IL-Fe3O4 MNPs as an efficient and green heterogeneous magnetic nanocatalyst for the one-pot three-component synthesis of highly substituted pyran derivatives under solvent-free conditions

The present study was conducted to synthesize Zr@IL-Fe3O4 MNPs as a new magnetically recoverable heterogeneous catalyst, which was then characterized by Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray spectroscopy (EDX), vibrating sample magnetometry (VSM), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) techniques. The catalytic behavior of the Zr@IL-Fe3O4 MNPs was efficiently used for the synthesis of highly substituted pyran derivatives via a one-pot three-component condensation of 4-hydroxycoumarin/dimedone, malononitrile, and arylaldehydes under solvent-free conditions. This new methodology demonstrated some important features, including short reaction times, excellent yields, lower loading of the catalyst, easy work-up, and recyclability of the catalyst for a minimum of six times without any noticeable decrease in catalytic activity.

One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight

The multicomponent synthesis of 1-amidoalkyl naphthols and polyhydroquinolines has been developed as an atom-economic procedure catalyzed by a deep eutectic solvent ([CholineCl][ZnCl2]3).

One-pot three-component synthesis of α-aminonitriles using sodium dihydrogen phosphate as a catalyst at room temperature

Sodium dihydrogen phosphate was applied as an efficient and inexpensive catalyst for the synthesis of biologically potent α-aminonitrile derivatives through a one-pot three-component reaction of aldehyde, amine and trimethylsilyl cyanide. The reactions were easily carried out under mild, green and eco-friendly conditions in ethanol at room temperature affording high yields of the products in short times.

One-Pot Three-Component Synthesis of 1-(α-Aminoalkyl)-2-Naphthols Using Nano-[Ni-4MSP](NO3)2 as a New Catalyst

7-amino-5-(4-methoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile was prepared as an amine and then reacted with salicylaldehyde and Ni(NO3)2.6H2O to afford nano–Ni-[4-methoxyphenyl-salicylaldimine-pyranopyrimidine dione] (NO3)2 {Nano-[Ni-4MSP](NO3)2} as a new Schiff base complex in nano size. Nano-[Ni-4MSP](NO3)2 as a new complexes was fully characterized by various analyses and successfully used as an effectual catalyst for the synthesis of some 1-( -Aminoalkyl)-2- naphthols.

Choline chloride-coated UiO-66-Urea MOF: A novel multifunctional heterogeneous catalyst for efficient one-pot three-component synthesis of 2-amino-4H-chromenes

A new Zr-based MOF, namely, UiO-66-Urea, was prepared through polymerization between the 2-aminoterephthalate linkers of UiO-66-NH2 MOF and 1,4-phenylene diisocyanate under mild reaction conditions. Post-synthetic coating of UiO-66-Urea with choline chloride (ChCl), as easily available, inexpensive, and nontoxic reagent, under thermal and solvent-free conditions resulted in in-situ formation of a deep-eutectic solvent-like on the UiO-66-Urea's surface, called here ChCl@UiO-66-Urea. The presence of Zr6O4(OH)4 nodes and urea groups may capable of strong hydrogen bond formation with ChCl. The porous and bioinspired ChCl@UiO-66-Urea was characterized using FT-IR, powder XRD, SEM, EDX elemental mapping, TGA, and BET surface area measurements. Choline chloride-coated UiO-66-Urea was successfully promoted one-pot three-component synthesis of 2-amino-4H-chromenes, as biologically active heterocycles, through reactions of aldehydes, malononitrile, and α-naphthol or 4-hydroxycoumarin under solvent-free conditions. The catalytic activity of the respective solid was superior than UiO-66, UiO-66-NH2, UiO-66-Urea, and even ChCl-2Urea due to synergistic effect between actives sites of UiO-66-Urea and ChCl. The reaction includes a consecutive three-step Knoevenagel condensation/Michael addition/cyclization mechanism.

Ultrasonically-mediated one-pot synthesis of substituted imidazoles via sulfamic acid functionalized hollow magnetically retrievable solid-acid catalyst

In this work, we report the synthesis of functionalized hollow magnetite spheres (HMS) which were synthesized through gas-bubble assisted Ostwald ripening approach and post-functionalized with sulfamic acid groups. The fabricated material was used as an efficient solid-acid catalyst for one-pot three-component synthesis of medicinally important tri-substituted imidazoles under ultrasonic irradiation. Some of the striking features of the present protocol over existing routes are environmentally benign synthesis, milder reaction conditions, excellent yields, high selectivity, short reaction times, use of ultrasound as green energy source, less waste generation and effortless magnetic recovery and recycling of the catalyst. Further, the synthesized magnetite spheres extend the scope of ‘double functionalization’, i.e., the acidic groups can be immobilized on both internal and external surfaces which provides high acid loading as compared to previously reported solid supports.

Clean 3,4-Dihydropyrimidones Synthesis via Biginelli Reaction over Supported Molybdenum: Structural and Textural Characteristic of αMoO3

A one-pot three-component synthesis of dihydropyrimidinones (DHPMs) via Biginelli reaction was carried out at 100 °C using benzaldehyde, ethyl acetoacetate and urea as reactants, in the presence of ethanol and free solvent, in heterogeneous catalytic medium. The Mo (30 wt%) metal oxides (Al2O3, SiO2 or MgO) used catalysts were prepared by sol-gel, impregnation and microemulsion methods and characterized by X-Ray Diffraction (XRD), Fourier Transform Infra Red (FTIR), Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-ray (EDX), Nitrogen Adsorption - Brunauer-Emmett-Teller (BET), and NH3-Temperature Programmed Desorption (TPD) methods. The Mo-SiO2 sample prepared by the sol-gel method exhibited the highest DHPM yield (87%), in free solvent with a reaction time of 30 min. The high efficiency, in the Biginelli reaction, of the Mo-SiO2 catalyst is due to its structural, textural and acid properties. Highly dispersed αMoO3 species of orthorhombic structure having a high contribution of strong acidic sites would be the active species in the Biginelli synthesis. Copyright © 2021 by Authors, Published by BCREC Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0).

Efficient one-pot three-component synthesis of 2H-indazole [2,1-b]phthalazine-1,6,11(13H)-triones at room temperature

Tetrabutylammonium bromide (TBAB) and cesium carbonate (Cs2O3) catalyzed, one-pot three-component synthesis of 2H-indazole[2,1b]phthalazine-1,6,11(13H)-triones was developed at room temperature in ethanol. Both electron donating and withdrawing groups are compatible under the optimized reaction parameters.