Pot Three-component Synthesis Research Articles

Expression of concern: An efficient one pot three-component nanocatalyzed synthesis of spiroheterocycles using TiO2 nanoparticles as a heterogeneous catalyst

Expression of concern for ‘An efficient one pot three-component nanocatalyzed synthesis of spiroheterocycles using TiO2 nanoparticles as a heterogeneous catalyst’ by Yogesh Kumar Tailor et al., RSC Adv., 2015, 5, 46415–46422, https://doi.org/10.1039/C5RA04863J.

Water Mediated One-Pot, Stepwise Green Synthesis, Anti-Inflammatory and Analgesic Activities of (3-Amino-1-Phenyl-1H-Benzo[f]Chromen-2-yl) (1H-Indol-3-yl) Methanone Catalysed by L-Proline

Aim: The reactions were carried out by one pot three-component synthesis, 3- cyanoacetylindole (1) on reaction with aromatic aldehydes (2) and β-naphthol (3) in an aqueous medium in the presence of L-proline as a catalyst under reflux for 30 min, resulting in (3-amino-1- phenyl-1H-benzo[f]chromen-2-yl) (1H-indol-3-yl)methanone (4). The method has many advantages like short reaction times, good yields, and simple workup procedure, besides being green in nature. Pharmacological evaluation of title compounds was done for anti-inflammatory and analgesic activities. Anti-inflammatory activity was carried carrageenan-induced paw edema model in which indomethacin was used as standard and analgesic activity was evaluated by eddy's hot plate method using diclofenac as standard drug. Background: Benzopyrans or chromenes are an important class of heterocyclic compounds due to their broad spectrum of biological activity and a wide range of applications in medicinal chemistry. The chromene moiety is found in various natural products with interesting biological properties. Chromenes constitute the basic backbone of various types of polyphenols and are widely found in alkaloids, tocopherols, flavonoids, and anthocyanins. Indoles are omnipresent in various bioactive compounds like alkaloids, agrochemicals, and pharmaceuticals. Objective: The objective of this study is to synthesize one-pot stepwise Green synthesis, antiinflammatory and analgesic activities of 3-amino-1-phenyl-1H-benzo[f]chromen-2-yl) (1H-indol-3- yl) methanones. Methods: The acute anti-inflammatory effect was evaluated by carrageenan-induced mice paw edema (Ma Rachchh et al., 2011). Edema was induced by injecting carrageenan (1% w/v, 0.1 ml) in the right hind paw of mice. The test compounds 1-12, indomethacin (10 mg/kg), and the vehicle were administered orally one hour before injection of carrageenan. Paw volume was measured with a digital plethysmometer at 0, 30, 60, 90, 120 min after injection. Percentage increase =A-B/ A *100 Results: Carrageenan induced paw edema model was used for anti-inflammatory activity in which animals treated with standard (indomethacin) and test compounds showed a significant decrease in the paw edema. Analgesic activity was estimated using Eddy’s hot plate method; animals were treated with standard (diclofenac) and test compounds showed a significant increase in the reaction time. Conclusion: A green, one-pot, step-wise and three-component synthesis of 3-amino-1-phenyl-1Hbenzo[ f]chromen-2-yl) (1H-indol-3-yl) methanone was achieved by using water as a solvent, Lproline as catalyst under reflux conditions. The reactions were carried out in eco-friendly conditions with shorter reaction times, easier workup, and high yields. Anti-inflammatory activity was evaluated by carrageenan-induced paw edema model, where significant anti-inflammatory activity is shown by all the test compounds 4(a-l) compared to standard drug. Analgesic activity was studied by Eddy’s Hot plate method and Test compounds 4e, 4f, 4h, 4i, 4j, 4k, 4l showed significant activities compared to the reference drug.

Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-Pyridazinediones as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria.

Pyridazine and thiazole derivatives have various biological activities such as antimicrobial, analgesic, anticancer, anticonvulsant, antitubercular and other anticipated biological properties. Chitosan can be used as heterogeneous phase transfer basic biocatalyst in heterocyclic syntheses. Novel 1-thiazolyl-pyridazinedione derivatives were prepared via multicomponent synthesis under microwave irradiation as ecofriendly energy source and using the eco-friendly naturally occurring chitosan basic catalyst with high/efficient yields and short reaction time. All the prepared compounds were fully characterized by spectroscopic methods, and their in vitro biological activities were investigated. The obtained results were compared with those of standard antibacterial/antifungal agents. DFT calculations and molecular docking studies were used to investigate the electronic properties and molecular interactions with specific microbial receptors.

Direct synthesis of regioselective α-allyl α-selanyl ketones and selanyl tetra-hydrofurans

An efficient approach for the synthesis of α-allyl α-selanyl ketone and selanyl tetrahydrofurans has been reported in this present work. The sodium methoxide (MeONa) mediated one pot three-component synthesis lead towards a good to an excellent yield of products with a wide substrate scope. The selenylated ketones can be important point towards important organic synthons.

Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1H-tetrazoles in water.

Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.

Retraction: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

Retraction of ‘An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions’ by Hongshe Wang et al., RSC Adv., 2019, 9, 5158–5163, DOI: 10.1039/C9RA00653B.

ZSM-5 catalyzed one pot three-component synthesis of 5-substituted-1H-tetrazoles from aldehyde

In this paper, we report one-pot three-component synthesis of 5-substituted-1H-tetrazoles from aldehyde using zeolite-based heterogeneous catalyst (ZSM-5). Wide functional group tolerance with high chemical yield has been achieved. Moreover, heterogeneous catalyst (ZSM-5) was recovered and reused several times without significant loss of its catalytic activity

Retracted Article: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

A simple and efficient protocol developed for one pot three-component synthesis of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate using the versatile super Brønsted acid triflimide (HNTf2) as an effective catalyst is described. The reactions proceed well in the presence of 1 mol% of HNTf2 at 80 °C under solvent-free conditions and provide the corresponding triarylpyridines in good to excellent yields. The method reported has several advantages such as a metal-free and commercially available catalyst, mild reaction conditions and lower loading of catalyst.

One pot three-component synthesis of 5-substituted 1H-tetrazole from aldehyde

A versatile, robust and efficient strategy for the synthesis of vast range of highly functionalized 5-substituted 1H-tetrazole derivatives by using one pot three-component synthesis from various aldehydes, hydroxylamine hydrochloride and sodium azide in presence of a catalytic amount of ceric ammonium sulphate, a non toxic, easily available, inexpensive, unexplored and reusable catalyst is reported. This one-pot synthesis has several advantages such as mild reaction conditions, shorter reaction time, low catalyst loading, good to moderate yields and functional group tolerance making this methodology practically feasible. The synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS.

One Pot Three-Component Synthesis of Thiazolidinone Derivatives of 4-Methylthiazole-5-carbaldehyde and its Biological Evaluation

One Pot Three-Component Synthesis of Thiazolidinone Derivatives of 4-Methylthiazole-5-carbaldehyde and its Biological Evaluation

Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents

BackgroundPyrazoles, thiazoles and 1,3,4-thiadiazoles have been reported to possess various pharmacological activities.ResultsAn efficient and a novel approach for the synthesis of some novel pyrazole based-azoles are described via multi-component reaction under controlled microwave heating conditions. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H NMR and mass spectral data. All the synthesized compounds were tested for in vitro activities against two antitumor cell lines, human lung cancer and human hepatocellular carcinoma compared with the employed standard antitumor drug (cisplatin).ConclusionsAll the newly synthesized compounds were evaluated for their anticancer activity against human lung cancer and human hepatocellular carcinoma cell lines using MTT assay. The results obtained exploring the high potency of six of the tested compounds compared with cisplatin. Graphical abstractMicrowave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents

A reactant promoted solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-thione analogues using ammonium thiocyanate

This is the first-time ammonium thiocyanate (NH4SCN) has been used as a self-promoting reactant for the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones. This report describes a greener, efficient and economic protocol for one pot three-component synthesis of Biginelli compounds using various aldehydes, β-ketoesters and ammonium thiocyanate. Ammonium thiocyanate being a weak acid, accelerate the rate of reaction to obtain Biginelli compounds in solvent-free condition at 110°C. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup and ability to tolerate a variety of functional groups. Ammonium thiocyanate is readily available, cheaper, safer and industrial acceptable material which gives economical as well as ecological rewards to the present method.

An efficient one pot three-component synthesis of dihydropyrano[3,2-c] chromenes using ammonium metavanadate as catalyst

An efficient one pot three-component synthesis of dihydropyrano[3,2-c] chromenes using ammonium metavanadate as catalyst

T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

An efficient methodology for the synthesis of 2,3-disubstituted 3H-quinazolin-4-ones is described via one-pot three component reaction from anthranilic acid using T3P as catalyst. Mild reaction conditions, short reaction time, broad functional group tolerance, easy isolation of products and good yields are main advantages of this protocol.

An efficient one pot three-component nanocatalyzed synthesis of spiroheterocycles using TiO2nanoparticles as a heterogeneous catalyst

An efficient, environmentally benign isocyanide-based domino protocol is presented for synthesizing spiroheterocycles with 2-amino benzothiazole/1,3,4-thiadiazole, cyclohexyl/tert-butyl isocyanides and isatines/cyclic carbonyls, catalyzed by recyclable nanocrystalline TiO2.

Efficient stepwise and one pot three-component synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)thiophene-3-carbonitriles

Environmentally benign conditions have been developed for the synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)thiophene-3-carbonitriles (3) starting from 3-acetyl-2H-chromen-2-one (1) through the intermediacy of 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)malononitrile (2) using the Knoevenagel condensation followed by the Gewald reaction. Alternatively, 3 could also be prepared in a one pot method by treating equimolar amounts of 1, malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions, easy work-up procedure, and good yields.

Zinc oxide nanoparticle promoted highly efficient one pot three-component synthesis of 2,3-disubstituted benzofurans

A convenient one-pot synthesis of 2,3-disubstituted benzo[b]furan derivatives has been developed using zinc oxide nanoparticles. The present approach provides a novel, effective and improved procedure for the three-component coupling of aldehydes, secondary amines and alkyne with several advantages such as short reaction times, high yields and little catalyst loading. ZnO nanoparticles are cheap, stable and can be easily recovered for several circles with consistent activity. Characterization and structural elucidation of the products have been done on the basis of chemical, analytical and spectral analyses.

Zinc triflate a water compatible, green catalyst in one pot three-component efficient synthesis of α-amino nitriles

Zinc triflate a water compatible, green catalyst in one pot three-component efficient synthesis of α-amino nitriles

Water promoted one pot three-component synthesis of tetrazoles

A one pot, three component synthesis of tetrazoles via thiourea has been accomplished in water. Water enhances the solubility of a higher number of components in the three component protocol thus promoting the reaction. The synthesis involves a chemoselective exocyclic reaction, regioselective electrocyclisation and a preferred conformational orientation of the tetrazole side chain which are rationalised based on the relative magnitude of Garbisch angle strain/allylic strains anticipated during the course of the reaction.

An efficient ultrasound-promoted one pot synthesis of spiroacenaphthylene pyrazolotriazole and pyrazolophthalazine derivatives

A facile and efficient one pot three-component ultrasound-promoted synthesis of spiro pyrazolo compounds has been developed. Employing ethanol as a solvent, assumed to be relatively environmentally benign, and use of an inexpensive and readily available catalyst combined with the advantages of sonochemistry, such as mild reaction conditions, excellent yield, and short reaction times highlight this synthetic route. The reactions were carried out under both conventional heating and ultrasound-assisted conditions and several reaction parameters are investigated and compared.