Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation

Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows: 1,5-diphenyl-1,4-pentadiene-3-one (1, 1 mmol), aminoguanidine hydrochloride (1.1 mmol), DBSA (0.5 mmol), water 10 mL, reaction temperature 25-27°C, irradiation frequency 25 kHz. 2a was achieved in 94% yield within 2h. The other seven amidinohydrazones were obtained in 84-94% yield within 2-3h under the same conditions. Compared to the method involving catalysis by hydrochloric acid in refluxing EtOH, the advantages of present procedure are milder conditions, shorter reaction times, higher yields, and environmental friendly conditions, which make it a useful strategy for the synthesis of analogues.     

Synthesis of alpha-oximinoketones under ultrasound irradiation

The reaction of 6-acylmethylphenanthridines with isoamyl nitrite results alpha-oximino-6-acylmethylphenanthridines in 73-95% yields in DMF under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.     

Synthesis of N-alkoxyphthalimides under ultrasound irradiation

The alkylation of N-hydroxyphthalimide with alkyl halides in the presence of potassium carbonate results N-alkoxyphthalimides in 64-99% yields in DMSO under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.     

Synthesis of oximes under ultrasound irradiation

The condensation of aldehydes and ketones with hydroxylamine hydrochloride results oximes in 50.7-98.7% yields in EtOH under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.     

Synthesis of ethyl α-cyanocinnamates under ultrasound irradiation

Knoevenagel condensation of ethyl cyanoacetate with aromatic aldehydes catalyzed by pyridine results ethyl α-cyanocinnamates in 80–96% yields under ultrasound irradiation.     

Resourceful synthesis of pyrazolo[1,5-a]pyrimidines under ultrasound irradiation

Pyrazolo[1,5-a]pyrimidines were synthesized via the ultrasonic sonochemical method using the cyclocondensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF₃C(O)CH = C(R)(OMe) – where R = Me, Bu, i-Bu, Ph, 4-Me–C₆H₄, 4-F–C₆H₄, 4-Cl–C₆H₄, 4-Br–C₆H₄, naphth-2-yl and biphen-4-yl] – with 3-amino-5-methyl-1H-pyrazole in the presence of EtOH for 5 min. This methodology has several advantages, for example, it is a simple procedure, it has an easy work-up, mild conditions, short reaction times (5 min) and produces satisfactory yields (61–98%).     

The solvent-free synthesis of 1,4-dihydropyridines under ultrasound irradiation without catalyst

The condensation of aldehydes, ethyl acetoacetate and ammonium acetate result 1,4-dihydropyridines in 82–99% yields under ultrasound irradiation without solvent and catalyst at room temperature. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.     

Synthesis of ethyl alpha-cyanocinnamates catalyzed by KF-Al2O3 under ultrasound irradiation

Knoevenagel condensation of ethyl cyanoacetate with aromatic aldehyde catalyzed by KF-Al2O3 in ethanol results ethyl alpha-cyanocinnamates in 97-99% yield under ultrasound irradiation.     

Synthesis of ethyl alkylidene alpha cyanoacetates under ultrasound irradiation

Condensation of ketones with ethyl cyanoacetate catalysed by ammonium acetate-acetic acid results in ethyl alkylidene alpha cyanoacetate in 31-89% yield under ultrasound irradiation.     

An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation

The condensation of aldehydes, beta-keto esters and urea catalyzed by NH(2)SO(3)H in ethanol results dihydropyrimidinones in high yields under ultrasound irradiation.     

Synthesis and characterization of Ag nanoparticles@Polyethylene fibers under ultrasound irradiation

The polyethylene fibers containing Ag nanoparticles were prepared through the chemical reduction under ultrasound irradiation. The effect of reducing reagent, power of ultrasound irradiation, reaction time and temperature in growth of the nanometric Ag were studied. Particle sizes and morphology of nanoparticle are depending on power of ultrasound irradiation. Results show a decrease in the particles size as increasing power of ultrasound irradiation. Also, an increase in temperature led to increase of particle size. The polyethylene fibers containing Ag nanoparticles were characterized with powder X-ray diffraction (XRD) and scanning electron microscopy (SEM).     

Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation

Synthesis of the glycolurils catalyzed by potassium hydroxide was carried out in 17–75% yield at 40 °C in EtOH under ultrasound irradiation. Compared to the method using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time.     

Synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones catalyzed by KF/basic Al2O3 under ultrasound

1,1-Disubstituted-2,6-diarylcyclohexane-4-ones have been synthesized via double Michael addition of 1,5-diaryl-1,4-pentadien-3-one with various active methylene compounds such as dimethyl malonate, diethyl malonate, methyl cyanoacetate and ethyl cyanoacetate catalyzed by KF/basic alumina under ultrasound irradiation to give good yields within a short time.     

An efficient synthesis of 3-substituted indole derivates under ultrasound irradiation

A solvent-free procedure for the synthesis of 3-substituted indole derivates from indoles and nitroalkenes under ultrasound irradiation is described. Control experiments disclosed besides mechanical effects, namely agitation, sonochemical effects are the main forces to drive the reaction. In the method, 2-chloroethanol was used to prepare a wide variety of 3-substituted indole derivates. This procedure only need equimolar amounts of reaction substrates and can be readily scaled up.     

Synthesis of new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones under catalyst-free and solvent-free conditions

Several new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones were synthesized via the three-component condensation reaction of aldehydes, aromatic amines, and ethyl pyruvate under catalyst-free and solvent-free conditions. Also, 5-(4-hydroxyl-3-nitrophenyl)-1-(4-methoxy-phenyl)-3-(4-methoxyphenylamino)-1,5-dihydro-pyrrol-2-one was synthesized using oxime instead of aldehyde. The eco-friendly, simple procedure, green procedure, catalyst-free and solvent-free conditions, short reaction times, and high yields of the products are the advantages of this method.     

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.     

Synthesis, crystal growth and characterization of 1,5-diphenylpenta-1,4-dien-3-one: An organic crystal

1,5-Diphenylpenta-1,4-dien-3-one ( dibenzalacetone, DBA) was synthesized by a base-catalyzed aldol condensation reaction between benzaldehyde and acetone. High quality single crystals have been grown by the slow evaporation of ethanol solution and the crystal belongs to monoclinic system with centrosymmetric space group C 2/c. The DBA crystals are transparent in the entire visible region and have a lower optical cutoff at ∼440 nm. It is stable up to 119 °C and has a good chemical stability. The high resolution X-ray diffraction curve (DC) indicates that the specimen is free from structural grain boundaries. Molecular packing leads to a centrosymmetric arrangement resulting in zero second harmonic generation (SHG; χ⁽²⁾=0) efficiency.     

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.     

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.     

Pinacol coupling of aromatic aldehydes and ketones using TiCl3-Mg under ultrasound irradiation

Titanium trichloride in EtOH can be reduced by Mg to the corresponding low valent titanium complexes, which can reduce some aromatic aldehydes and ketones to the corresponding pinacols in 8-95% yields within 15-40 min under ultrasound irradiation.