One-Pot Four-Component Research Articles

Base-Promoted One-Pot Four-Component Domino Strategy Involving Aldehydes and Ketones to Access Multifunctionalized Dihydropyridinones.

The synthesis of multifunctionalized dihydropyridinones from aldehydes and ketones involves at least a three-step process, making route shortening a challenging task, especially in achieving a one-pot four-component synthesis via aldehydes and ketones precondensation. Herein, we discovered a [1 + 2 + 1 + 2] four-component domino cyclization reaction, a novel concept in 4CRs with commercially available ketones and aldehydes, which by initially combining aldehydes and ketones with Meldrum's acid and ammonium acetate (NH4OAc), respectively, they give dihydropyridones (>110 examples). This transformation features inexpensive additives and readily available starting materials, making it appropriate for rapid access to relevant pharmaceutical molecules containing dihydropyridinone-derived heterocycles. Also these compounds can be conveniently converted into trisubstituted and tetrasubstituted pyridines.

Perfluoroalkyl-Decorated Noble-Metal-Free MOFs for the Highly Efficient One-Pot Four-Component Coupling between Aldehydes, Amines, Alkynes, and Flue Gas CO2.

The non-noble-metal catalysed-multicomponent reactions between flue gas CO2 and cheap industrial raw stocks into high value-added fine chemicals is a promising manner for the ideal CO2 utilization route. To achieve this, the key fundamental challenge is the rational development of highly efficient and facile reaction pathway while establishing compatible catalytic system. Herein, through the stepwise solvent-assisted linker installation, post-synthetic fluorination and metalation, we report the construction of a series of perfluoroalkyl-decorated noble-metal-free metal-organic frameworks (MOFs) PCN-(BPY-CuI)-(TPDC-Fx ) [BPY=2,2'-bipyridine-5,5'-dicarboxylate, TPDC-NH2 =2'-amino-[1,1':4',1''-terphenyl]-4,4''-dicarboxylic acid] that can catalyze the one-pot four-component reaction between alkyne, aldehyde, amine and flue gas CO2 for the preparation of 2-oxazolidinones. Such assembly endows the MOFs with superhydrophobic microenvironment, superior water resistance and highly stable catalytic site, leading to 21 times higher turnover numbers than that of homogeneous counterparts. Mechanism investigation implied that the substrates can be efficiently enriched by the MOF wall and then the adsorbed amine species act as an extrinsic binding site towards dilute CO2 through their strong preferential formation to carbamate acid. Moreover, density functional theory calculations suggest the tetrahedral geometry of Cu in MOF offers special resistance towards amine poisoning, thus maintaining its high efficiency during the catalytic process.

Microwave-Assisted IBX-Mediated One-Pot Four-Component Synthesis of 4-Arylhexahydroquinoline Derivatives from Benzyl Alcohols: A Metal-Free Approach

Microwave-Assisted IBX-Mediated One-Pot Four-Component Synthesis of 4-Arylhexahydroquinoline Derivatives from Benzyl Alcohols: A Metal-Free Approach

An Efficient and Green Synthesis of New 6-Iodo- Pyrano[2,3-d] Pyrimidine-4-Ones via a One-Pot Four-Component Reaction Followed by Iodocyclization in Water

Eco-friendly one-pot synthesis of new 6-iodo-4H-pyrano[2,3-d]pyrimidin-4-ones via the condensation of pyrimidine-4,6-diol, aldehydes, phenylacetylene, and iodine has been reported in water at 60 °C. To obtain the optimal reaction conditions, the effects of reaction temperature, bases and solvents were investigated. Under the optimal condition, formaldehyde and different aromatic aldehydes bearing both electron-donating and withdrawing groups underwent the reaction to give the corresponding 6-iodo-5,7-disubstituted-3H-pyrano[2,3-d] pyrimidin-4(5H)-one derivatives in high to excellent (90–97%) yields. This transformation generates 6-iodo-4H-pyrano[2,3-d]pyrimidin-4-one derivatives using a domino reaction involving Knoevenagel condensation and iodocyclization in the absence of metal or acidic/basic catalysts. The prepared products were characterized using FT-IR, 1HNMR, 13CNMR, and Mass spectroscopies.

A One-Pot Four-Component Procedure for the Synthesis of Dispiro[tetrahydroquinoline-bis(2,2-dimethyl-1,3-dioxane-4,6-dione)] Derivatives

A One-Pot Four-Component Procedure for the Synthesis of Dispiro[tetrahydroquinoline-bis(2,2-dimethyl-1,3-dioxane-4,6-dione)] Derivatives

An Efficient One-Pot Four-Component Synthesis of 9-Aryl-Hexahydroacridine-1,8-Dione Derivatives in the Presence of a Molecular Sieves Supported Iron Catalyst

A series of 9-aryl-hexahydroacridine-1,8-diones are synthetized with good to excellent yields (50–99%) via a one-pot four-component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of 4 Å molecular sieves modified with iron(III) as an efficient heterogeneous catalyst, in ethanol. The process offers the advantages of high yields, mild reaction conditions and easy work-up procedure. The catalyst can be reused without significant loss of activity.Graphic

Direct Allylation of Aliphatic Primary Amines via Al(OTf)3-Catalyzed One-Pot Four-Component Reaction

Direct Allylation of Aliphatic Primary Amines via Al(OTf)₃-Catalyzed One-Pot Four-Component Reaction

Tartaric Acid: A Naturally Green and Efficient Di-Functional Brønsted Acid Catalyst for the One-Pot Four-Component Synthesis of Polysubstituted Dihydropyrrol-2-Ones at Ambient Temperature

A series of biologically active polysubstituted dihydropyrrol-2-ones are prepared via a one-pot four-component reaction of structurally diverse dialkyl acetylenedicarboxylate, formaldehyde, and amines (aromatic and aliphatic) using a catalytic amount of tartaric acid as a naturally green, mild di-functional Bronsted acid catalyst at ambient temperature. The use of tartaric acid as an inexpensive catalyst makes this procedure eco-friendlier and also one-pot, easily separated from the reaction mixture, good to high yields, short reaction times, simple operational procedures, and highly efficient that are the added advantages of the present methodology.

Alkaline-Earth-Catalyzed sp3 C–H Functionalization of Methyl Azaarenes and Its Use in a One-Pot Four-Component Synthesis of Azaarenyl Benzylpyrazolones

The sp³ C–H functionalization of methyl azaarenes by using calcium triflate as the catalyst is described, together with its use in the first synthesis of azaarenyl benzylpyrazolones by a one-pot four-component reaction.

Ionic Liquids as Carbene Catalyst Precursors in the One-Pot Four-Component Assembly of Oxo Triphenylhexanoates (OTHOs)

Ionic liquids (ILs) are a convenient and inexpensive source of N-heterocyclic carbenes (NHCs). In this study, dialkyl imidazolium-based ILs are used as carbene precursors in a four-component synthesis of oxo triphenylhexanoates (OTHOs), where it was found that IL outperformed commonly used NHC precatalysts in terms of reaction efficiency. The reaction is highly stereoselective, delivering the anti-diastereomer (20:1 dr), and the OTHOs can be obtained in high-to-excellent yields. By virtue of the four-component reaction-setup, facile construction of the OTHO scaffold with a diverse set of functional groups (21 examples) can be achieved. In the context of sustainability, the IL can be recovered and reused several times without affecting selectivity or yield. Moreover, most compounds can be isolated by precipitation and filtration, mitigating the use of solvent-demanding chromatography.

ChemInform Abstract: Facile, Efficient and Diastereoselective Synthesis of α‐Hydrazine Tetrazoles Through a Novel One‐Pot Four‐Component Reaction.

AbstractThe title tetrazole derivatives are obtained by a new Ugi four‐component reaction of hydrazides (I), cyclic ketones (II), trimethylsilyl azide, and the corresponding isocyanide without any catalyst in a one‐pot procedure.

A Xylose-Catalyzed One-Pot Four-Component Domino Protocol for the Facile Synthesis of Highly Substituted Dihydropyrrol-2-ones

Xylose is a natural, cheap, and efficient organocatalyst for the synthesis of the title compounds (V) (21 examples) via a four-component domino reaction between amines, dialkyl acetylenedicarboxylates, and formaldehyde.

Efficient One-Pot Four-Component Synthesis and X-ray Crystallographic Structure of 2-Pyridone Derivatives

A series of 3-cyano-2-pyridone derivatives were synthesized by one-pot four-component condensation reaction involving a benzaldehyde derivative, alkyl cyanoacetate, acyclic or cyclic ketones, and ammonium acetate in reflux condition. The X-ray structure of the products 5a and 5d confirm symmetric dimers via hydrogen bonding interactions between individual pyridine molecules showing, in addition, also π–π stacking interactions.

An Efficient One-Pot Four-Component Hantzsch Reaction to Prepare Hydroquinolines Catalyzed by a Poly(ethylene glycol) Bridged Dicationic Basic Ionic Liquid under Solvent-Free Conditions

A piperidine-functionalized poly (ethylene glycol) bridged dicationic ionic liquid PEG800-DPIL(Cl) was synthesized and applied to catalyze the four-component Hantzsch reaction under solvent-free conditions and afford hydroquinolines with high to excellent yields. PEG800-DPIL(Cl) could be recovered by simple workup and recycled for at least eight times without obvious activity loss.

Microwave-Assisted Copper(II)-Catalyzed One-Pot Four-Component Synthesis of Multifunctionalized Dihydropyridines

A fast and highly efficient copper-catalyzed multicomponent synthesis of 1,4-dihydropyridines under microwave irradiation is described. The protocol utilizes mild reaction conditions with low catalytic loading, leading to high yields. This methodology provides us with biologically active 1,4-dihydropyridine library for medicinal chemistry applications.

Ru(II)-catalyzed chemo- and regioselective cyclotrimerization of three unsymmetrical alkynes through boron temporary tether. One-pot four-component coupling via cyclotrimerization/Suzuki-Miyaura coupling.

The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki-Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53-76% yields.