Improved synthesis of chalcones under ultrasound irradiation

Claisen-Schmidt condensation of acetophenone with aromatic aldehydes catalyzed by pulverized KOH and KF-Al2O3 results chalcones in 52-97% and 83-98% yields respectively in alcoholic solvent under ultrasound irradiation.     

A facile synthesis of pyridazinone derivatives under ultrasonic irradiation

A new, efficient and general method for preparation of N-substituted-pyridazinones using ultrasound irradiation is reported. Under ultrasound the reaction time decreases substantially, the yields are high and the reaction conditions are mild. It was noticed that substituents at the 3-(6)-position of pyridazone heterocycle have a substantial influence on the reactivity, while the effect of the substituents at the 1-(2)-position seems to be of minor importance. A comparative study of the reactions performed under ultrasound conditions versus at room temperature has been done.     

Improved synthesis of chalconoid-like compounds under ultrasound irradiation

Claisen–Schmidt condensation of various substituted acetophenones with cinnamaldehyde catalyzed by KF–Al₂O₃ results chalconoid-like compounds, (2E,4E)-1,5-diarylpenta-2,4-dien-1-ones, in 67–92% yields in 5–60 min under ultrasound irradiation.     

Rapid and efficient synthesis of fused heterocyclic pyrimidines under ultrasonic irradiation

Some fused heterocyclic pyrimidines have been synthesized in high yields using ultrasound irradiation in a one-pot, three-component and efficient process by condensation reaction of barbituric acids, aldehydes and a series of enamines in water. Prominent among the advantages of this new method are operational simplicity, good yields in short reaction times and easy work-up procedures employed.     

1-Methylimidazolium hydrogen sulfate catalyzed convenient synthesis of 2,5-dimethyl-N-substituted pyrroles under ultrasonic irradiation

Ionic liquid [HMIM]HSO₄ was found to be an efficient catalyst for the synthesis of N-substituted pyrroles through the reaction of 2,5-hexanedione with amines under ultrasonic irradiation at room temperature. These reactions proceed with good yields under short reaction time. Furthermore, the green catalytic system can be recycled specific times with no decreases in yields and reaction rates.     

The synthesis of allyl ether functionalized siloxane monomers under ultrasonic irradiation at ambient conditions

The novel class of cationic UV-curable allyl ether functionalized siloxane monomers type CH₂=CH---CH₂---O---R---O---Si(CH₃)₃ and type CH₂=CH---CH₂---O---R---O---Si(CH₃)₂---O---R---CH₂---CH=CH₂ have been synthesized in excellent yields in short times at ambient temperature conditions in the absence of any added catalyst by the classical silylation reactions of homoallyloxyalcohols with chlorosilanes under ultrasonic irradiation.     

An expeditious synthesis of beta-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation

PTSA catalyzes the Michael addition of indole to alpha,beta-unsaturated carbonyl ketones under ultrasonic irradiation to afford the corresponding product beta-indolylketones in excellent yields (up to 94%).     

Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles

The ionic liquid 1-ethyl-3-methylimidazole acetate ([EMIM]OAc) was found to be a mild and effective catalyst for the efficient, one-pot, three-component synthesis of 2-aryl-4,5-diphenyl imidazoles at room temperature under ultrasonic irradiation. This procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, reacting at room temperature, high yields, simplicity of the methodology.     

Improved synthesis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation

Diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates (1) have been synthesized by the reaction of aryl aldehyde and 1,3-diketone catalyzed by ZnCl₂ under ultrasound irradiation. The effects of changes in the ultrasonic power, temperature, and reaction time are discussed. With the optimized reaction conditions, various aryl aldehydes were used to synthesize 4H-pyrans (1) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time and high yield of product.     

CaCl2 as a bifunctional reusable catalyst: diversity-oriented synthesis of 4H-pyran library under ultrasonic irradiation

CaCl₂ is applied as an efficient reusable and eco-friendly bifunctional catalyst for the one-pot three-component synthesis of 4H-pyrans under ultrasonic irradiation. A broad range of substrates including the aromatic and heteroaromatic aldehydes, indoline-2,3-dione (isatin) derivatives, acenaphthylene-1,2-dione (acenaphthenequinone) and 2, 2-dihydroxy-2H-indene-1,3-dione (ninhydrin) were condensed with carbonyl compounds possessing a reactive ??-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The catalyst could be recycled and reused several times without any loss of efficiency.     

Effect of ultrasonic irradiation power on sonochemical synthesis of gold nanoparticles

In this work, optimized size distribution and optical properties in the colloidal synthesis of gold nanoparticles (GNPs) were obtained using a proposed ultrasonic irradiation assisted Turkevich-Frens method. The effect of three nominal ultrasound (20 kHz) irradiation powers: 60, 150, and 210 W have been analyzed as size and shape control parameters. The GNPs colloidal solutions were obtained from chloroauric acid (HAuCl₄) and trisodium citrate (C₆H₅Na₃O₇·2H₂O) under continuous irradiation for 1 h without any additional heat or stirring. The surface plasmon resonance (SPR) was monitored in the UV–Vis spectra every 10 min to found the optimal time for localized SPR wavelength (${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$), and the 210 sample procedure has reduced the ${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$ localization at 20 min, while 150 and 60 samples have showed ${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$ at 60 min. The nucleation and growth of GNPs showed changes in shape and size distribution associated with physical (cavitation, temperature) and chemical (radical generation, pH) conditions in the aqueous solution. The results showed quasi-spherical GNPs as pentakis dodecahedron (${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$ = 560 nm), triakis icosahedron (${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$ = 535 nm), and tetrakis hexahedron (${\lambda }_{\mathrm{L}\mathrm{S}\mathrm{P}\mathrm{R}}$ = 525 nm) in a size range from 12 to 16 nm. Chemical effects of ultrasound irradiation were suggested in the disproportionation process, electrons of AuCl₂⁻ are rapidly exchanged through the gold surface. After AuCl₄⁻ and Cl⁻ were desorbed, a tetrachloroaurate complex was recycled for the two-electron reduction by citrate, aurophilic interaction between complexes AuCl₂⁻, electrons exchange, and gold seeds, the deposition of new gold atoms on the surface promoting the growth of GNPs. These mechanisms are enhanced by the effects of ultrasound, such as cavitation and transmitted energy into the solution. These results show that the plasmonic response from the reported GNPs can be tuned using a simple methodology with minimum infrastructure requirements. Moreover, the production method could be easily scalable to meet industrial manufacturing needs.     

An efficient and practical synthesis of mandelic acid by combination of complex phase transfer catalyst and ultrasonic irradiation

Mandelic acid was synthesized from benzaldehyde with chloroform in a 81% yield at 60 degrees C for 2 h by using triethylbenzylammonium chloride (TEBA) and poly(ethylene glycol)-800 (PEG-800) as a complex phase transfer catalyst under ultrasonic irradiation. The main advantages of this present method are that the reaction time is much shorter and the yield is higher than those of the classical method. p-Methoxymandelic acid was also obtained in a 84% yield under the same reaction conditions.     

Sonocatalytic degradation of acid red B and rhodamine B catalyzed by nano-sized ZnO powder under ultrasonic irradiation

Nano-sized ZnO powder was introduced to act as the sonocatalyst after the treatment of high-temperature activation, and the ultrasound of low power was used as an irradiation source to induce nano-sized ZnO powder performing sonocatalytic degradation of acid red B and rhodamine B. At the same time, the effects of operational parameters such as solution pH value, initial concentration of dyestuff and addition amount of nano-sized ZnO powder have been examined in this paper. We found that the degradation ratios of acid red B and rhodamine B in the presence of nano-sized ZnO powder were much higher than that with only ultrasonic irradiation. However, the degradation ratio of acid red B was about two times higher than that of rhodamine B for the initial concentration of 10.0 mg/L, addition amount of 1.0 g/L nano-sized ZnO powder, solution acidity of pH 7.0 and 60 min irradiation experimental condition. The difference of the degradation ratios can be illustrated by the difference of chemical forms of acid red B and rhodamine B in aqueous solution and the surface properties of nano-sized ZnO particles. In addition, the researches on the kinetics of sonocatalytic reactions of acid red B and rhodamine B have also been performed and found to the follow pseudo first-order kinetics. All the experiments indicated that the sonocatalytic method in the presence of nano-sized ZnO powder was an advisable choice for the treatments of non- or low-transparent organic wastewaters in future.     

Application of ultrasonic irradiation to the sol-gel synthesis of silver vanadium oxides

An ultrasonic irradiation method was applied to the sol-gel synthesis of silver vanadium oxides (SVO). Transmission electron microscope (TEM), X-ray diffraction (XRD), thermogravimetry (TG) and differential thermal analysis (DTA) were conducted to research the ultrasonically accelerated reaction between V2O5 gel and Ag2O powder. Galvanostatic discharge experiments showed that the as prepared cathode active material of Ag2V4O11 and Ag(1.2)V3O8 have better electrochemical properties than those synthesized by conventional solid state method.     

A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation

Fe₃O₄ nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe₃O₄ nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology.     

Destruction of polylactic acid microcapsules under ultrasound irradiation

Hollow microcapsules have been considered for potential applications as drug or gene carriers. This paper describes an investigation into the mechanical properties of microcapsules with a biocompatible polylactic acid (PLA) shell that can be destroyed using ultrasound irradiation. The microcapsules had a radius of 1 to 25 μm and a shell thickness of 100 nm to 3 μm, and their response to ultrasound pulses with a center frequency of 700 kHz to 2 MHz was investigated. It was found that approximately 50% of capsules with a radius of 20 μm were destroyed using pulses with a pressure amplitude of 50 kPa and a frequency of 700 kHz, which is close to the resonance frequency of the capsules.     

Introduction of poly(4-vinylpyridinium) perchlorate as a new,efficient, and versatile solid acid catalyst for one-pot synthesis of substituted coumarins under ultrasonic irradiation

Poly(4-vinylpyridinium) perchlorate, is a supported, recyclable, eco-benign catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. The catalyst was studied by FT-IR, X-ray diffraction, scanning electron microscope, thermo-gravimetric and energy dispersion X-ray analyses. All the products were extensively characterized by ¹H NMR, FT-IR, MS and melting point analyses. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times without loss of activity.     

Preparation of a water-soluble fullerene [C70] under ultrasonic irradiation

A water-soluble fullerene [C(70)] is prepared with fullerene [C(70)] and a mixture of concd. sulfuric acid (H(2)SO(4)) and concd. nitric acid (HNO(3)) at the ratio (v/v) of 3:1 under ultrasonic irradiation at 25-43 degrees C. The MALDI-TOF-MS spectra confirmed that the product of a water-soluble fullerene compound was C(70).     

An efficient enzymatic modification of cordycepin in ionic liquids under ultrasonic irradiation

A comparative study of the immobilized Candida antarctica lipase B (Novozym 435)-catalyzed acylation of cordycepin with vinyl acetate in ionic liquids (ILs) under ultrasonic irradiation and shaking was conducted. The application of ultrasonic irradiation instead of shaking during acylation resulted in an enhanced reaction rate and a higher level of substrate conversion. Among the various ILs examined, 1-butyl-3-methylimidazolium tetrafluorobrate ([C₄MIm][BF₄]) was the best medium for the reaction because it produced the highest substrate conversion. In [C₄MIm][BF₄], the optimal ultrasonic power, water activity, and reaction temperature were 120 W, 0.33, and 50 °C, respectively. The acylation of cordycepin in [C₄MIm][BF₄] proved to be regioselective under both conditions: the C5′-OH was acylated. Novozym 435 exhibited a much higher operational stability in [C₄MIm][BF₄], and 58.0% of its original activity was maintained after ten reuse cycles under ultrasonic irradiation. Compared with the cordycepin, the rate of adenosine deaminase-catalyzed deamination was greatly reduced when the 5′-OH was substituted by acetyl group. These results demonstrated that the combined application of ultrasonic irradiation and IL as a medium was an efficient approach for the enzymatic modification of cordycepin.     

One-pot synthesis of benzylacetamide from oxime under ultrasound irradiation

One-pot synthesis of benzylacetamide from oxime can be carried out in 80–95% yield at 35–40 °C under ultrasound irradiation. This method provided several advantages such as simple work-up procedure, shorter reaction time and higher yield.