Synthesis Of Polyhydroquinoline Derivatives Research Articles

One-pot synthesis of polyhydroquinoline derivatives using nano-Fe3O4@dextrin/BF3 as a magnetic biodegradable catalyst

One-pot synthesis of polyhydroquinoline derivatives using nano-Fe3O4@dextrin/BF3 as a magnetic biodegradable catalyst

Efficient one‐pot synthesis of polyhydroquinoline derivatives through the Hantzsch condensation using IRMOF‐3 as heterogeneous and reusable catalyst

AbstractA mesoporous Zn‐based 2‐amino terephthalate metal organic framework (IRMOF‐3) catalyst was prepared using the solvothermal method. The synthesized catalyst was characterized by powder X‐ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive spectroscopy (EDAX), and Brunauer–Emmett–Teller surface area analysis (BET). It was applied as an effective heterogeneous catalyst for the synthesis of one‐pot four‐component polyhydroquinoline derivatives via the Hantzsch condensation. The present method offers several advantages over other reported methods such as easy separation, mild reaction condition, and excellent yield of desired product. Furthermore, the catalyst can be reused without loss in activity.

Novel marine‐based gold nanocatalyst in solvent‐free synthesis of polyhydroquinoline derivatives: Green and sustainable protocol

We report an ecofriendly synthetic approach for the fabrication of biogenic gold nanoparticles (AuNPs) using electron‐rich sea cucumber extract as a bio‐reductant and stabilizing agent in reducing gold cations into AuNPs at the optimal conditions. The produced AuNPs are spherical in shape with an average particle size of 11 ± 1.5 nm in transmission electron microscopy (TEM) and exhibited a crystal structure of face‐centered cubic in X‐ray diffraction (XRD) analyses. Our results indicated that bioinspired AuNPs demonstrate superior catalytic activity in the safe and facile one‐pot synthesis of polyhydroquinoline derivatives under solvent‐free reaction conditions. This green route encompasses multiple benefits including highly recyclable bioinspired catalyst (5 cycles), short reaction times, convenient workout, high to excellent product yields (82%–97%), and nonhazardous conditions.

New Copper Complex on Fe3O4 Nanoparticles as a Highly Efficient Reusable Nanocatalyst for Synthesis of Polyhydroquinolines in Water

In this work, we present a simple, environmentally friendly and economical route for the preparation of a novel copper-Schiff-base organometallic complex on Fe3O4 nanoparticles (Fe3O4@Schiff-base-Cu) using an inexpensive and simple method and available materials. This magnetic nanocatalyst was comprehensively characterized using Fourier transform infrared spectroscopy (FT-IR), X-Ray Diffractometer (XRD), inductively coupled plasma atomic emission spectroscopy (ICP), energy-dispersive X-ray spectroscopy (EDS), scanning electron microscopy (SEM), X-ray mapping, thermogravimetric analysis (TGA) and vibrating sample magnetometer (VSM) analysis. In the second stage, the catalytic activity of this catalyst was studied in the synthesis of polyhydroquinoline derivatives via Hantzsch reaction in water as a green solvent. In this sense, simple preparation of the catalyst from the commercially available materials, high catalytic activity, simple operation, short reaction times, high yields and use of green solvent can be regarded as some advantages of this protocol. In addition, it is worth mentioning that this nanocatalyst was easily recovered using external magnet and reused for several times without significant loss of its catalytic efficiency. Finally, the leaching, heterogeneity and stability of Fe3O4@Schiff-base-Cu were studied by hot filtration test and ICP technique. A green and novel Fe3O4@Schiff-base-Cu catalyst sucssesfully was prepared and characterized. This catalyst can be used for the Synthesis of polyhydroquinolines in water as the green solvent. This catalyst could be recovered easily and reused many times without important decrease in efficiency.

Covalent immobilization of Co complex on the surface of SBA-15: Green, novel and efficient catalyst for the oxidation of sulfides and synthesis of polyhydroquinoline derivatives in green condition

In this work, a green and novel catalyst was prepared through immobilization of cobalt complex on the surface of mesostructured SBA-15 and characterized by TGA, SEM, FT‐IR, EDX, ICP, BET and X-ray mapping analytical methods. This mesostructural material was used as an efficient and green interphase catalyst for the oxidation reactions and synthesis of polyhydroquinoline derivatives. All reactions were performed in short times and good yields. Moreover, the prepared catalyst could be used up to six runs without significant degradation in its catalytic activity or cobalt leaching.

Nickel(II) immobilized on dithizone–boehmite nanoparticles: as a highly efficient and recyclable nanocatalyst for the synthesis of polyhydroquinolines and sulfoxidation reaction

In this work, in the first stage, boehmite nanoparticles were easily fabricated via addition of NaOH solution to a solution of Al(NO3)3.9H2O at room temperature in water. Then, nickel–dithizone catalyst was supported on boehmite nanoparticles (Ni-dithizone@boehmite). Ni-dithizone@boehmite is a low-cost, nontoxic, and recoverable catalyst, which provides an environment friendly reaction conditions. In the second stage, catalytic activity of this catalyst was studied in the synthesis of polyhydroquinoline derivatives and selective oxidation of sulfides to sulfoxides. The reactions not require very high temperatures or inert atmosphere. The developed heterogeneous catalyst could be easily separated by centrifugation and recycled for several runs without leaching of Nickel from the surface of the catalyst or significant loss of its catalytic activity.

One‐Pot Synthesis of Polyhydroquinoline Derivatives through Organic‐Solid‐Acid‐Catalyzed Hantzsch Condensation Reaction

AbstractWe report the synthesis of a new porous polymeric network (PPN) using triphenylamine and α,α‐dibromo‐p‐xylene by a Friedel–Crafts alkylation promoted by anhydrous FeCl3 as an oxidizing agent. Sulfonation of PPN led to a sulfonated porous polymeric network (SPPN) having high surface acidity and high BET surface area. We characterized the PPN and SPPN materials thoroughly by using powder XRD, FTIR spectroscopy, 13C solid‐state magic‐angle spinning NMR, field‐emission SEM, high‐resolution TEM, and N2 sorption techniques. The sulfonated material SPPN was then employed as a heterogeneous, reusable, and environmentally benign organic solid‐acid catalyst for the one‐pot synthesis of biologically important polyhydroquinoline derivatives under microwave irradiation.

S‐Benzylisothiourea complex of palladium on magnetic nanoparticles: A highly efficient and reusable nanocatalyst for synthesis of polyhydroquinolines and Suzuki reaction

S‐Benzylisothiourea complex of palladium supported on modified Fe3O4 magnetic nanoparticles (Pd‐SBTU@Fe3O4) is reported for carbon–carbon coupling through the Suzuki coupling reaction. Also, the synthesis of polyhydroquinoline derivatives is reported in the presence of Pd‐SBTU@Fe3O4 as nanocatalyst. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, vibrating sample magnetometry and inductively coupled plasma atomic emission spectroscopy. The nanocatalyst was easily recovered using an external magnet and reused several times without significant loss of its catalytic efficiency. The heterogeneity of Pd‐SBTU@Fe3O4 was studied using hot filtration.

Synthesis, characterization and heterogeneous catalytic application of a nickel(II) Schiff base complex immobilized on MWCNTs for the Hantzsch four-component condensation

A nickel(II) Schiff base complex immobilized on multi-wall carbon nanotubes (MWCNTs) surface as a highly efficient heterogeneous catalyst was synthesized and characterized by IR, X-ray diffraction patterns, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma, elemental analysis, and thermal gravimetric analysis. Then a facile and environmentally benign procedure was developed for synthesis of polyhydroquinoline derivatives via Hantzsch one-pot condensation reaction of aromatic aldehydes, 1,3-diones, ethyl acetoacetate, and ammonium acetate in the presence of above synthesized catalyst under solvent-free conditions. This protocol has the advantages of stability, easy availability, recyclability and eco-friendly nature of catalyst, simple experimental and work-up procedure, and also high to excellent yields. Considering the solvent-free condition and also temperature, time, and yield of the model reaction, the nanocatalyst reported here is among the best catalysts reported so far for synthesis of polyhydroquinolines.

Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives

A simple, efficient, and environmentally benign protocol for the synthesis of polyhydroquinoline derivatives was developed using a bio-compatible, heterogeneous, and recoverable mesoporous ionic liquid supported nanoporous silica as a nano-catalyst. The polyhydroquinoline derivatives were obtained by the four-component reaction of aldehyde, Meldrum’s acid, dimedone, and ammonium acetate in excellent yields .

Cu(II) Schiff Base Complex as a Highly Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation in Water

In the present study, Cu(II) Schiff-base complex is introduced as a highly efficient and green solid catalyst for the unsymmetrical Hantzsch condensation through a four-component coupling of various aldehydes, dimedone, ethyl acetoacetate and ammonium acetate to form polyhydroquinoline derivatives in good to excellent yields. This reaction was carried out in the presence of 1 mol% of catalysts in water at room temperature. The reusability of the catalysts was demonstrated by a five-run test. Remarkable features of this new procedure are cleaner reaction profiles, shorter reactiontimes, simple experimental and work-up procedures.

Synthesis of polyhydroquinoline derivatives via a four-component Hantzsch condensation catalyzed by tin dioxide nanoparticles

Tin dioxide (SnO 2 ) nanoparticles efficiently catalyzed unsymmetrical four-component Hantzsch condensations of various aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate to form polyhydroquinoline derivatives in excellent yields. This novel method offers several advantages over the traditional method of synthesizing these compounds, including safety, mild conditions, short reaction times, high yields, and an easy workup. A simple procedure for the SnO 2 nanoparticle-catalyzed preparation of polyhydroquinoline derivatives in aqueous ethanol at ambient temperature is described.

ZnO-nanoparticle-promoted synthesis of polyhydroquinoline derivatives via multicomponent Hantzsch reaction

Zinc oxide nanoparticles are used as an effective and reusable catalyst for one-pot, four-component couplings of aldehydes, dimedone, active methylene compounds, and ammonium acetate to produce polyhydroquinoline derivatives under solvent-free conditions at room temperature. Compared with other methods, satisfactory results are obtained with high yields, short reaction times, and simplicity in the experimental procedure. The catalyst could easily be recycled and reused four times without noticeable decrease in catalytic activity.

ChemInform Abstract: Efficient One‐Pot Synthesis of Polyhydroquinoline Derivatives Using Silica Sulfuric Acid as a Heterogeneous and Reusable Catalyst under Conventional Heating and Energy‐Saving Microwave Irradiation.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Nickel Nanoparticle Catalyzed Facile and Efficient One‐Pot Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation under Solvent‐Free Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Sulfamic Acid Catalyzed One-Pot Synthesis of Polyhydroquinolines via the Hantzsch Four Component Condensation Reaction

The synthesis of polyhydroquinoline derivatives has been achieved using catalytic amounts of green, inexpensive and environmentally benign sulfamic acid. The process is operationally simple and has good to excellent yields.

ChemInform Abstract: Facile ZrCl4 Promoted Four‐Component Coupling One‐Pot Synthesis of Polyhydroquinoline Derivatives Through Unsymmetric Hantzsch Reaction.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of polyhydroquinoline derivatives under aqueous media without catalyst

Synthesis of polyhydroquinoline derivatives under aqueous media without catalyst

5-Pyrrolidin-2-yltetrazole-Promoted One-Pot Hantzsch Polyhydroquinoline Synthesis Using NH4HCO3 as Nitrogen Source

A straightforward and green synthesis of polyhydroquinoline derivatives was reported via a four-component coupling reaction of aldehydes, dimedone, active methylene compounds, and ammonium bicarbonate in the presence of 5-pyrrolidin-2-yltetrazole under solvent-free conditions. The method offers several advantages including high yields, an environmental friendly procedure, a short reaction time, and easy isolation of products.

Solvent-free liquid-phase synthesis of polyhydroquinoline derivatives under microwave irradiation

Polyhydroquinoline derivatives have been efficiently prepared on polyethylene glycol (PEG) via one-pot condensation of PEG-bound acetoacetate, 1,3-cyclohexanedione, ammonium acetate and the appropriate aromatic aldehyde in the presence of catalytic amounts of polyphosphoric acid by solvent-free microwave irradiation. The procedure provided the target compounds in excellent yield and purity with a facile work-up procedure.