Three-component Processes Research Articles

WITHDRAWN: Green Synthesis and Evaluation of the Biological Activity of New Dihydropyridine Derivatives

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Oxidative Three-Component Selenofunctionalization of Alkenes: Convenient Access to Vicinally Functionalized Selenides

Three-component selenofunctionalization processes of olefins, diselenides and sulfonamides, water, alcohols, or acids utilizing 1-fluoropyridinium triflate (FP-OTf) as a reaction promoter are reported. Under the optimal conditions, a broad range of vicinally functionalized selenide derivatives was accessible with high yields and excellent functional group compatibilities. Mechanistic studies revealed that the FP-OTf played a key role in this selenofunctionalization process.

Palladium-Catalyzed Three-Component Coupling Reaction via Benzylpalladium Intermediate.

Transition-metal catalyzed multi-component reactions have captured the attention of researchers in organic synthesis and drug synthesis due to their advantages of simple operation, easy availability of raw materials and without separation of intermediates. Among the multi-component reactions, the three-component processes have been developed into effective organic procedures. This personal account reviews our and other group's studies on the development of three-component coupling reaction for the rapid construction of two new chemical bonds simultaneously via benzylpalladium intermediates. Catalyst-switched three-component reactions of benzyl halides, activated olefins, and allyltributylstannane were successfully conducted to produce the corresponding benzylallylation products. Activation and conversion of carbon monoxide and carbon dioxide via π-benzylpalladium intermediates provide access to a wide range of unsaturated ketones and esters with excellent functional group tolerance. Meanwhile, other methods to produce benzylpalladium intermediates, including Heck insertion of alkenes into arylpalladium complexes, the oxidative addition of benzyl carbonate to palladium complexes and palladium-carbene migratory insertion, were also highlighted.

Nickel-catalyzed site- and stereoselective reductive alkylalkynylation of alkynes

Nickel-catalyzed site- and stereoselective reductive alkylalkynylation of alkynes

Widely Electronically Tunable 2,6-Disubstituted Dithieno[1,4]thiazines-Electron-Rich Fluorophores Up to Intense NIR Emission.

2,6‐Difunctionalized dithieno[1,4]thiazines were efficiently synthesized by (pseudo)five‐ or (pseudo)three‐component one‐pot processes based on lithiation‐electrophilic trapping sequences. As supported by structure–property relationships, the thiophene anellation mode predominantly controls the photophysical and electrochemical properties and the electronic structures (as obtained by DFT calculations). From molecular geometries and redox potentials to fluorescence quantum yields in solution, the interaction of the dithieno[1,4]thiazine‐core with the substituents causes striking differences within the series of regioisomers. Most interestingly, strong acceptors introduced in anti–anti dithieno[1,4]thiazines nearly induce a planarization of the ground‐state geometry and a highly intense NIR fluorescence (ΦF=0.52), whereas an equally substituted syn–syn dithieno[1,4]thiazine exhibits a much stronger folded molecular structure and fluoresces poorly (ΦF=0.01). In essence, electrochemical and photophysical properties of dithieno[1,4]thiazines can be tuned widely and outscore the compared phenothiazine with cathodically shifted oxidation potentials and redshifted and more intense absorption bands.

Solvent-free synthesis of 1-amidoalkyl-2-naphthols using magnetic nanoparticle-supported 2-(((4-(1-iminoethyl)phenyl)imino)methyl)phenol Cu (II) or Zn (II) Schiff base complexes

Two magnetic nanoparticle-supported 2-(((4-(1-iminoethyl)phenyl)imino)methyl)phenols were successfully synthesized, characterized, and applied in the one-pot three-component reaction of substituted benzaldehydes, 2-naphthol, and amides for synthesis of 1-amidoalkyl-2-naphthols. These three-component processes occurred under solvent-free reaction conditions at 80 °C. The magnetically recoverable supported Schiff base metal catalysts can be reused several times in the model reaction. The synthesized catalysts are also easily separated from the reaction mixture by applying an external magnet. This procedure offers the advantages of simple, operational procedure as well as no use of hazardous organic solvents.

Sulfanilic Acid-catalyzed Synthesis of 4-arylidene-3-substituted isoxazole-5(4H)-ones

Aim and Objective: In recent studies, chemistry of heterocyclic compounds, especially isoxazoles, has been widely considered by organic chemistry researchers because they have been found in many molecules, including naturally occurring bioactive compounds, pharmaceuticals, and agrichemicals. Isoxazol- 5(4H)-ones and their derivatives, on the other hand, have significant biological properties can be mentioned as examples of antibacterial, anti-inflammatory, antifungal, anticancer, analgesic, fungicidal, and insecticidal activities. Therefore, the development of ecofriendly methods, such as three-component processes, for the synthesis of isoxazol-5(4H)-ones is highly desirable. This work focus on the one-pot, three-component reaction (3-CR) of aldehydes, hydroxylamine hydrochloride, and three β-ketoester using catalytic amounts of sulfanilic acid (SA) aimed at the synthesis of isoxazol-5(4H)-ones. Another aim of this study is to use water as a green solvent for the above-mentioned 3-CR. <p> Materials and Methods: Using SA as an efficient organocatalyst, the multicomponent cyclocondensation of aromatic/hetero-aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/ethyl 4- chloroacetoacetate/ethyl benzoylacetate has been implemented. The reactions were carried out in water as a green solvent at room temperature. The corresponding heterocyclic products were separated by simple filtration and washing with water. Also, the solvent was removed from the filtrate by evaporation to recycle the catalyst. Results: It was found that SA act as the catalyst for the synthesis of 4-arylidene-3-substituted isoxazole-5(4H)- ones via three-component reaction of aromatic/hetero-aromatic aldehydes, hydroxylamine hydrochloride, and three β-dicarbonyl compounds (ethyl acetoacetate, ethyl 4-chloroacetoacetate, and ethyl benzoylacetate). Optimization of the catalyst quantity and solvent showed that the highest yield was achieved with 20 mol% of SA in aqueous media. 4-Arylidene-3-substituted isoxazole-5(4H)-ones have been successfully synthesized in the presence of SA catalyst. Conclusion: The SA catalyst could be recovered easily from the filtrate via evaporation of solvent and reused many times. The present synthetic method is a simple, green, clean, and environmentally friendliness alternative for synthesizing 4-arylidene-3-substituted isoxazole-5(4H)-ones. Reactions were performed without the use of heating, microwave and ultrasound irradiations.

K2CO3/cyanuric acid catalyzed synthesis of 2-amino-4H-chromene derivatives in water

Three-component processes for the synthesis of 2-amino-4H-chromenes catalyzed by potassium carbonate/cyanuric acid in water as a safe solvent were developed. These reactions were performed at room temperature through one-pot reactions. The benefits of this research are short reaction time, excellent yield, clean reaction media, simple work-up and easy purification.

Multi-physics modeling of flow and transport in porous media using a downscaling approach

Multi-phase flow and transport processes generally occur on different spatial and temporal scales. Very often also, within a physical system, they vary in space meaning that different kinds of processes might take place in different parts of the system. In order to account for the variety of processes and to take their scale-dependence into account, the development of multi-scale multi-physics techniques can be envisaged. We extend a recently developed multi-scale multi-physics algorithm by Niessner and Helmig [Niessner J, Helmig R. Multi-scale modeling of three-phase–three-component processes in heterogeneous porous media. Adv Water Resour 2007;11(30):2309–25] where concentration equations were solved in a small part of the domain on a fine scale while pressure and saturation distribution were solved for in the whole physical system. While the saturation equation was upscaled to a coarser scale the pressure equation was still solved time-implicitly and on a fine scale. The new extension of this work is the upscaling of the pressure equation also. Where needed a downscaling approach provides fine-scale velocities. In this technical note, comparisons of the extended algorithm to the original one and to a fine-scale reference solution are shown. The major benefits of this extension are more flexibility with respect to the choice of scale and computational efficiency (the time-implicit solution of the fine-scale pressure equation is very costly) while maintaining a high accuracy.

Iron-Catalyst-Switched Selective Conjugate Addition of Grignard Reagents: α,β,γ,δ-Unsaturated Amides as Versatile Templates for Asymmetric Three-Component Coupling Processes

Diene für konjugierte Additionen: Eisen(II)- chlorid ändert den Verlauf der Dreikomponentenkupplung eines Grignard-Reagens mit einem Alkylhalogenid und einem Dienamid. Das Amid wirkt dabei als einfaches und zugleich vielseitiges chirales Templat.

Multi-scale modeling of three-phase–three-component processes in heterogeneous porous media

Flow and transport processes in porous media occur on different spatial and temporal scales and may also be locally different. Additionally, the structure of the porous medium itself generally shows a high dependence on the spatial scale. As an example, the contamination of the unsaturated zone with a light non-aqueous phase liquid is studied, corresponding to a domain with randomly distributed heterogeneities where complex three-phase–three-component processes are relevant only in a small (local) subdomain. This subdomain needs fine resolution as the complex processes are governed by small-scale effects. For a comprehensive fine-scale model taking into account three-phase–three-component processes as well as heterogeneities in the whole (global) model domain, data collection is expensive and computational time is long. Therefore, we developed a general multi-scale concept where on the one hand, the global flow field influences the local three-phase–three-component processes on the fine-scale. On the other hand, a coarse-scale saturation equation is solved where the effects of the fine-scale multi-phase–multi-component processes in the subdomain are captured by source/sink terms and the effects of fine-scale heterogeneities by a macrodispersion term. It turned out that the new multi-scale algorithm represents a flexible and extendable tool for incorporating processes of different complexity occurring at different locations in one model domain, while reducing the amount of required data. Using a simplified numerical example, it could be shown that the multi-scale algorithm functions very well. However, more research has to be done in order to further improve its computational efficiency.

Stable Tetravalent Phosphonium Enolate Zwitterions

Stable Tetravalent Phosphonium Enolate Zwitterions

The Azaallylic Anion as a Synthon for Pd‐Catalyzed Synthesis of Heterocycles: Domino Two‐ and Three‐Component Synthesis of Indoles

Piecing it all together with palladium: Two- and three-component cascade processes that are promoted by a multifunctional Pd catalyst lead to indoles in a highly efficient manner (see scheme). The key step is the Pd-catalyzed α-arylation of imines with o-dihalobenzene derivatives.

Combined Experimental and Computational Investigation of the Mechanism of Nickel-Catalyzed Three-Component Addition Processes

Combined Experimental and Computational Investigation of the Mechanism of Nickel-Catalyzed Three-Component Addition Processes

Dialogicality and social representations: the dynamics of mind

Preface 1. An epistemological problem for social psychology 2. Thinking and antinomies 3. Linguistic and dialogical antinomies 4. Thinking through the mouth 5. Social representations: old and new 6. Dialogical triads and three-component processes 7. Understanding themata and generating social representations Conclusion: social representations and dialogicality.

Combined Experimental and Computational Investigation of the Mechanism of Nickel-Catalyzed Three-Component Addition Processes

The mechanism of nickel-catalyzed couplings of an enone, alkyne, and organozinc has been studied. Adducts of the substrates with nickel(0) have been isolated and characterized, and their reactivity was examined. A potential intermediate was demonstrated to not be kinetically competent in catalytic cyclizations. A computational approach employing the B3LYP density functional method and the 6-31G(d) basis set was used to examine mechanistic possibilities that were consistent with experimental observations, and a modified mechanism for the catalytic cyclizations was formulated. The newly proposed mechanism involves production of an active catalyst that involves a novel interaction between Ni(0) and dimethylzinc.

Three‐Component Processes for the Synthesis of 4‐Aryl‐7,7‐dimethyl‐5‐oxo‐3,4,5,6,7,8‐hexahydrocoumarin in Aqueous Media.

ChemInformVolume 35, Issue 21 Heterocyclic Compounds Three-Component Processes for the Synthesis of 4-Aryl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin in Aqueous Media. Daqing Shi, Daqing Shi Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorJing Chen, Jing Chen Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorQiya Zhuang, Qiya Zhuang Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorHongwen Hu, Hongwen Hu Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this author Daqing Shi, Daqing Shi Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorJing Chen, Jing Chen Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorQiya Zhuang, Qiya Zhuang Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this authorHongwen Hu, Hongwen Hu Dep. Chem., Xuzhou Norm. Univ., Xuzhou 221009, Peop. Rep. ChinaSearch for more papers by this author First published: 29 April 2004 https://doi.org/10.1002/chin.200421123Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume35, Issue21May 25, 2004 RelatedInformation

Three-component processes for the synthesis of 4-aryl-7,7-dimethyl- 5-oxo-3,4,5,6,7,8-hexahydrocoumarin in aqueous media

The reaction of an aromatic aldehyde, isopropylidene malonate and 5,5-dimethyl-1,3-cyclohexanedione in water in the presence of triethylbenzylammonium chloride (TEBA) as catalyst affords a one-pot synthesis of 4-aryl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin.

Multicomponent Domino Process to Oxa‐Bridged Polyheterocycles and Pyrrolopyridines, Structural Diversity Derived from Work‐up Procedure.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure

Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine ( 3 ), an aldehyde ( 4 ) and an α-isocyanoacetamide ( 5 ) in methanol at room temperature provides an efficient access to oxa-bridged tricycle ( 1 ) as a single diastereoisomer. In this one-pot process, one C–N, one C–O and three C–C bonds are formed with concomitant creation of five asymmetric centers. While isolable, the oxa-bridged tricycles ( 1 ) can be cleanly in-situ fragmented to pyrrolopyridines ( 2 ) under acidic conditions (trifluoroacetic acid, −78°C), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chemical yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis.