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AbstractZSM-5, an efficient and reusable heterogeneous catalyst, is employed for the one-pot, three-component synthesis of 2,4,6-triarylpyridines from substituted benzaldehydes, acetophenones and ammonium acetate using a simple, efficient, and green method. Both electron-releasing and withdrawing aldehydes and ketones went smoothly into substituted 2,4,6-triarylpyridines. Notably, the present reaction was carried out in the solvent-fee condition. The key merits of the present protocol are the milder reaction condition, easy workup protocol, high yield of desired pyridines and recyclability and reusability of the catalyst. The developed protocol offers a broad scope of substrate applicability and good sustainability. [ABSTRACT FROM AUTHOR]

In this study, we demonstrate the successful synthesis of sulfur–MOF composites and their application in the Willgerodt–Kindler reaction. We showed that MIL-53(Al), CAU-10-H and MIL-101(Cr) encapsulate the sulfur without MOF decomposition by the melt-diffusion technique, whereas MIL-88A and MIL-101(Fe) were unable to form S@MOF composites. Various techniques, including XRD, SEM, EDS, and porometry, were used to characterize the synthesized S@MOF composites. The influence of MOF nature, temperature, reaction time and reagent ratio on the Willgerodt–Kindler reaction product formation was evaluated. The S@CAU-10-H composite led to the thiomorpholides from various arylaldehydes, acetophenones and propiophenones in 56–91% isolated yields. The reaction proceeds at near equimolar reactant concentrations. Product isolation is straightforward and does not require tedious chromatographic purification. The MOF was easily separated and reused in five runs, achieving a good performance without significant framework degradation. We postulate that the MOF has multiple roles, acting as a reaction medium, sulfur carrier, amine absorber and dehydration agent. [ABSTRACT FROM AUTHOR]

The efficient and promising solvent-free method, catalyzed by Sulphated Tin oxide (SO42-/SnO2), has been developed for the synthesis of 1,3,5-triarylbenzene and its derivatives. The Bronsted acidic surfactant catalyst facilitates quick results and high yields, offering additional advantages such as easy separation and reusability with almost the same efficiency for subsequent cycles. This protocol involves the self-condensation of three molecules through cyclotrimerization with high chemo-selectivity. The substrate methyl phenyl ketone contains both electronwithdrawing and electron-donating groups, which assemble the target moiety with high and low yields, respectively. The synthesized compounds are evaluated through in silico studies to assess their drug-likeness properties. [ABSTRACT FROM AUTHOR]

The main building blocks for the production of flavonoids and iso-flavonoids are chalcones. Chalcones are α, β-unsaturated carbonyl compounds containing three carbons. The condensation products of aromatic aldehydes with acetophenones in the presence of a catalyst are called chalcones. Numerous techniques and plans have been documented for the synthesis of these substances. Aldol condensation and Claisen–Schmidt condensation continue to hold a prominent position among all. Chalcones and their derivatives have a broad range of pharmacological activities due to presence of reactive α,β-unsaturated carbonyl group. Numerous chalcone-heterocycle hybrids seem to show promise as potential medication candidates based on a review of the literature because of their comparable or better activity than the standards. As a result, the creation and development of novel, highly effective therapeutic medications based on previously established techniques may benefit from this review. [ABSTRACT FROM AUTHOR]

The density, viscosity and sound velocity of the binary liquid mixtures of P-methyl acetophenone with cyclohexylamine, cyclohexanol, and cyclohexane are measured over the complete composition range at temperatures of 303.15–313.15 K and at atmospheric pressure of 0.1 M. Excess molar volume, excess isentropic compressibility and viscosity deviation are calculated from the experimental measurements. The sign and magnitude of the derived parameters reveal the nature and type of interactions between the constituent molecules in the binary mixtures. Thermodynamic properties for this work reveal association interactions between dissimilar molecules in the binary systems P-methyl acetophenone + cyclohexylamine and P-methyl acetophenone + cyclohexanol systems, whereas dispersion forces cause the opposite trend in the other binary system P-methyl acetophenone + cyclohexane. [ABSTRACT FROM AUTHOR]

In Search of new antibacterial, antifungal agents with improved potency, herein we report the synthesis of a series of new substituted 2-(4-fluorophenyl)-3-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)-4H-chromen-4-one derivatives (6a‐q), starting from acetophenone. All the synthesized compounds have been screened for in vitro antibacterial and antifungal activity by using the agar well diffusion method. Among fifteen synthesized compounds, four chromone derivatives i.e. (6a-b), (6h), and (6i) have shown proficient antimicrobial activities. Compound (6a) showed powerful inhibitory activity against all bacterial pathogens but it was not that effective against fungal pathogens on the other hand compound (6b) showed satisfactory activity against fungal pathogens as well. The activity of compounds (6h) and (6i) against S. aureus was remarkable. Other compounds were found active against a few pathogens but activity was good. The compound (6b) was found very effective in inhibiting the growth of S. aureus ATCC 6538 at a low concentration with MIC 190 µg/ml. [ABSTRACT FROM AUTHOR]

In this work, LaMnO3 was prepared by the sol-gel method followed by thermal treatment. The catalytic activity of LaMnO3 in the synthesis of 2-henylbenzo[d]imidazo[2,1-b]thiazole (2-PIT) from 2-aminobenzothiazole and acetophenone was strongly influenced by the calcination temperature. The highest efficiency of samples synthesized at 800◦C was approved due to Lewis acid and oxygen vacancy sites properties which were confirmed through NH3-TPD and H2-TPR. Furthermore, the stability and reusability of the sample demonstrated the potential of LaMnO3 heterogeneous catalysts in organic synthesis applications.

This review will primarily focus on recent methods employed for the synthesis of a diverse array of chalcones with broad-ranging biological activities, with a particular emphasis on the past five years. The utilization of aromatic methyl ketones and their derivatives as starting materials for the synthesis of various heterocyclic compounds, such as chalcones, pyrazolines, dioxolanes, aminothiazoles, and more, holds significant importance in the field of synthetic organic chemistry. The synthesized heterocyclic compounds can serve as valuable subjects for testing to assess their biological activity.

A magnetic nanocomposite based on graphene oxide was prepared. Fe3O4 nanoparticles were loaded on graphene oxide sheets and GO-Fe3O4 was covered by aniline-pyrrol copolymer to afford poly(Ani-co-Py)@GO-Fe3O4 nanocomposite. The poly(Ani-co-Py)@GO-Fe3O4 nanocomposite was characterized by FT-IR, TEM, VSM, TGA, XRD, and EDX techniques and applied in the synthesis of 2,4,6-triarylpyridines derivatives via four-component reaction of various benzaldehydes, acetophenones, and ammonium. The absence of solvent, high yields of products, short reaction times, mild reaction conditions, and easy work-up procedure in combination with non-toxicity, efficiency, high surface area, stability, cheapness, magnetic character, and reusability of the catalyst are noteworthy advantages of the present method. [ABSTRACT FROM AUTHOR]

Acetophenones are naturally occurring phenolic compounds which have found in over 24 plant families and also fungi strains. They are exist in both free or glycosides form in nature. The biological activities of these compounds have been assayed and reported including cytotoxicity, antimicrobial, antimalarial, antioxidant and antityrosinase activities. Herein, we review the chemistry and biological activity of natural acetophenone derivatives that have been isolated and identified until January 2024. Taken together, it was reported 252 acetophenone derivatives in which the genera Melicope (69) and Acronychia (44) were the principal species as producers of acetophenones. [ABSTRACT FROM AUTHOR]

An improved design is described for ferroelectric crystals and implemented with the "methoxyphenyl series" of acetophenone azines, (MeO−Ph, Y)‐azines with Y=F (1), Cl (2), Br (3), or I (4). The crystal structures of these azines exhibit polar stacking of parallel beloamphiphile monolayers (PBAMs). Azines 1, 3, and 4 form true racemates whereas chloroazine 2 crystallizes as a kryptoracemate. Azines 1–4 are helical because of the N−N bond conformation. In true racemates the molecules of opposite helicity (M and P) are enantiomers A(M) and A*(P) while in kryptoracemates they are diastereomers A(M) and B*(P). The stacking mode of PBAMs is influenced by halogen bonding, with 2–4 showcasing a kink due to directional interlayer halogen bonding, whereas fluoroazine 1 demonstrates ideal polar stacking by avoiding it. Notably, (MeO−Ph, Y)‐azines display a stronger bias for dipole parallel alignment, attributed to the linearity of the biphenyl moiety as compared to the phenoxy series of (PhO, Y)‐azines with their non‐linear Ph−O−Ph moiety. The crystals of 1–4 all feature planar biphenyls and this synthon facilitates their crystallization through potent triple T‐contacts and enhances their nonlinear optical (NLO) performance by increasing conjugation length and affecting favorable chromophore conformations in the solids. [ABSTRACT FROM AUTHOR]

The mechanisms of the Cp*IrIII(bpyOO)‐catalyzed (bpyOO=bidentate (NN) doubly deprotonated 2,2′‐bipyridine‐6,6′‐diol) acceptorless methanol dehydrogenation and acetophenone transfer hydrogenation by methanol under basic conditions have been explored by the combination of 1H NMR, kinetics, and DFT computational studies. During dehydrogenation of methanol and of its dehydrogenated derivatives, the presence of two iridium hydride species (anionic [Cp*Ir(bpyOO)H]−, C* and neutral [Cp*Ir(bpyOOH)H], D*), which interconvert depending on pH, was detected. The DFT studies on a Cp model system highlighted three interrelated catalytic cycles of methanol, formaldehyde and formic acid dehydrogenation, all leading to the same hydride intermediates C and D. The dehydrogenation of methanol prefers a direct β‐hydride transfer pathway from the methoxide ion to Ir, rather than the classical β‐hydride elimination pathway from a coordinated methoxide ligand, but an alternative bifunctional H+/H− transfer with involvement of a ligand O atom may become competitive at lower pH. The transfer hydrogenation of acetophenone using methanol as hydrogen source features species C* as resting state, with the acetophenone reduction being rate‐determining and following the reverse pathway of methanol oxidation, with a first‐order acetophenone decay and a kinetic isotope effect of 2.36±0.09. [ABSTRACT FROM AUTHOR]

Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction of pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This reaction involved the formation of C–N and C–C bonds and new indolizine compounds with high stereoselectivity and excellent functional group tolerance. [ABSTRACT FROM AUTHOR]

• PdPtV nanoparticles (NPs) are synthesized using the oil-phase co-reduction strategy. • The PdPtV/CeO 2 −ZrO 2 catalyst performs the best in ethylbenzene (EB) oxidation. • PdPtV/CeO 2 −ZrO 2 shows large EB adsorption capacity, good reducibility, and strong surface acidity. • TPD and in situ DRIFTS are used to study the reversible poisoning of PdPtV/CeO 2 −ZrO 2 by SO 2. • V doping to PdPt NPs protects the active PdPt sites from being poisoned by SO 2. The PdPtVO x /CeO 2 −ZrO 2 (PdPtVO x /CZO) catalysts were obtained by using different approaches, and their physical and chemical properties were determined by various techniques. Catalytic activities of these materials in the presence of H 2 O or SO 2 were evaluated for the oxidation of ethylbenzene (EB). The PdPtVO x /CZO sample exhibited high catalytic activity, good hydrothermal stability, and reversible sulfur dioxide-poisoning performance, over which the specific reaction rate at 160°C, turnover frequency at 160°C (TOF Pd or Pt), and apparent activation energy were 72.6 mmol/(g Pt ⋅sec) or 124.2 mmol/(g Pd ⋅sec), 14.2 sec−1 (TOF Pt) or 13.1 sec−1 (TOF Pd), and 58 kJ/mol, respectively. The large EB adsorption capacity, good reducibility, and strong acidity contributed to the good catalytic performance of PdPtVO x /CZO. Catalytic activity of PdPtVO x /CZO decreased when 50 ppm SO 2 or (1.0 vol.% H 2 O + 50 ppm SO 2) was added to the feedstock, but was gradually restored to its initial level after the SO 2 was cut off. The good reversible sulfur dioxide-resistant performance of PdPtVO x /CZO was associated with the facts: (i) the introduction of SO 2 leads to an increase in surface acidity; (ii) V can adsorb and activate SO 2 , thus accelerating formation of the SO x 2− (x = 3 or 4) species at the V and CZO sites, weakening the adsorption of sulfur species at the PdPt active sites, and hence protecting the PdPt active sites to be not poisoned by SO 2. EB oxidation over PdPtVO x /CZO might take place via the route of EB → styrene → phenyl methyl ketone → benzaldehyde → benzoic acid → maleic anhydride → CO 2 and H 2 O. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract The α-bromination reaction of carbonyl compounds is a significant topic in the field of organic chemistry. However, due to the lack of suitable brominating reagents, the application of this reaction in undergraduate organic chemistry experiments is limited. In this study, three junior undergraduates successfully conducted an innovative experiment under the guidance of teachers. The bromination of various acetophenone derivatives was investigated by employing pyridine hydrobromide perbromide as the brominating agent, with a focus on exploring the effects of reaction time, reaction temperature, and dosage of the brominating agent. The results demonstrated that 4-chloro-α-bromo-acetophenone could be synthesized at 90 ℃ using 4-chloroacetophenone as a substrate and acetic acid as a solvent with a molar ratio of substrate to brominator being 1.0:1.1. Through the experimental teaching of 18 junior undergraduates, it was observed that all the students successfully completed the experiment within a time frame of 4–5 h, with a notable achievement yield exceeding 80% observed in 14 students. This innovative experiment exhibits significant advantages in terms of safety, high yield, cost-effectiveness, and repeatability. Furthermore, while reinforcing fundamental skills in chemistry experimentation among students, it enhances their scientific literacy levels and fosters innovation consciousness as well as practical aptitude. Consequently, this approach is highly suitable for widespread implementation and integration into undergraduate experimental pedagogy.

This work presents a simple approach for the synthesis of 2‐amino‐3‐cyanopyridines via a one pot two‐step sequential route catalysed by direct N‐−SO3H functionalised Brønsted acidic ionic liquids (BAILs). Herein, catalytic activities of four BAILs namely ([TSPi][Cl]2, [DSIM][TFA], [EDSIM][TFA] and [DBDSA][TFA]) were explored and among them [TSPi][Cl]2 was found to be the most efficient reusable homogeneous catalyst. This process involves the ionic liquid catalysed in situ generation of chalcones from Claisen‐Schmidt condensation between aromatic aldehydes and acetophenone/4‐Cl acetophenone, followed by multicomponent reaction (MCR) with malononitrile and ammonium acetate using the same IL catalyst to selectively produce 2‐amino‐3‐cyanopyridine derivatives in a solvent‐free medium at 80 °C within 30–60 minutes in high yields (96–86 %). This amalgamation of MCR with ionic liquids and solvent‐free conditions makes the present work more compliant with the protocols of Green Chemistry. [ABSTRACT FROM AUTHOR]

The species Senecio nutans Sch. Bip., commonly called "chachacoma", is widely used as a medicinal plant by the Andean communities of Northern Chile. Ethanolic extracts of S. nutans and the main compound, 4-hydroxy-3-(3-methyl-2-butenyl) acetophenone, have shown interesting biological activity. However, due to the high-altitude areas where this species is found, access to S. nutans is very limited. Due to the latter, in this work, we carried out micropropagation in vitro and ex vitro adaptation techniques as an alternative for the massive multiplication, conservation, and in vitro production of high-value metabolites from this plant. The micropropagation and ex vitro adaptation techniques were successfully employed, and UHPLC-DAD analysis revealed no significant changes in the phenolic profile, with acetophenone 4 being the most abundant metabolite, whose antioxidant and antibacterial activity was studied. Independently of the applied culture condition, the ethanolic extracts of S. nutans presented high activity against both Gram-positive and Gram-negative bacteria, demonstrating their antimicrobial capacity. This successful initiation of in vitro and ex vitro cultures provides a biotechnological approach for the conservation of S. nutans and ensures a reliable and consistent source of acetophenone 4 as a potential raw material for pharmacological applications. [ABSTRACT FROM AUTHOR]

A convenient protocol for the synthesis of 25,26,27-tribenzoyl-28-[((S)-1-diphenylphos- phanyl-propan-2-yl)oxy]-calix[4]arene via stereospecific methylation on Evans' oxazolidinone moiety was reported. According to the 13C NMR analysis of this phosphine, the calix[4]arene skeleton adopted a 1,3-alternate conformation. The latter conformation of the macrocycle and the (S)-chirality of the carbon atom bearing the methyl substituent were confirmed by a single-crystal X-ray diffraction study. After coordination of the phosphinated ligand to the dimeric [RuCl2(p-cymene)]2 organometallic precursor, the resulting arene–ruthenium complex was tested in the asymmetric reduction of acetophenone and alcohol was obtained with modest enantiomeric excess. [ABSTRACT FROM AUTHOR]

Background Tramadol (TRM) and celecoxib (CLX) form a novel mixture that helps relieve acute pain when other painkillers have no action. It is also reported that these drugs, TRM and CLX, are used to control COVID-19 symptoms. Objective The current work highlights three important pillars of modern pharmaceutical analysis, which are as follows; impurity profiling, greenness/whiteness studies and simplicity accompanied by sensitivity. Since 4-methyl acetophenone inhibits the human carbonyl reductase enzyme (type I) and since this compound may pose a health risk, it is crucial to regulate its concentration in all dosage forms of CLX. Methods Two simple and green spectrophotometric methods were developed, namely third derivative (D3) and Fourier self- deconvulation (FSD), for resolving severely overlapped spectra of TRM and CLX in the presence of 4-methyl acetophenone (4-MAP) as a process-related impurity in their novel tablet combination. Results The two approaches showed acceptable linearity with an excellent correlation coefficient. In both methods, TRM was measured when CLX and 4-methyl acetophenone were zero-crossing. The same procedure was applied for measuring CLX and its process-related impurity 4-MAP. Conclusion The methodologies developed were thoroughly validated in compliance with ICH (International Council on Harmonisation) guidelines. Student t - and F -tests revealed no statistically significant variation among the current methods and the reported method. Highlights No spectrophotometric methods have been published previously for the simultaneous analysis of TRM and CLX along with 4-MAP. As a result, the newly developed spectrophotometric approaches have great relevance and originality in the field of pharmaceutical analysis. [ABSTRACT FROM AUTHOR]

The α-bromination reaction of carbonyl compounds is a significant topic in the field of organic chemistry. However, due to the lack of suitable brominating reagents, the application of this reaction in undergraduate organic chemistry experiments is limited. In this study, three junior undergraduates successfully conducted an innovative experiment under the guidance of teachers. The bromination of various acetophenone derivatives was investigated by employing pyridine hydrobromide perbromide as the brominating agent, with a focus on exploring the effects of reaction time, reaction temperature, and dosage of the brominating agent. The results demonstrated that 4-chloro-α-bromo-acetophenone could be synthesized at 90 ℃ using 4-chloroacetophenone as a substrate and acetic acid as a solvent with a molar ratio of substrate to brominator being 1.0:1.1. Through the experimental teaching of 18 junior undergraduates, it was observed that all the students successfully completed the experiment within a time frame of 4–5 h, with a notable achievement yield exceeding 80% observed in 14 students. This innovative experiment exhibits significant advantages in terms of safety, high yield, cost-effectiveness, and repeatability. Furthermore, while reinforcing fundamental skills in chemistry experimentation among students, it enhances their scientific literacy levels and fosters innovation consciousness as well as practical aptitude. Consequently, this approach is highly suitable for widespread implementation and integration into undergraduate experimental pedagogy. [ABSTRACT FROM AUTHOR]

The Indian meal moth, Plodia interpunctella (Lepidoptera: Pyralidae), a globally distributed storage pest, relies on odors that are emitted from stored foods to select a suitable substrate for oviposition. However, the molecular mechanism underlying the chemical communication between P. interpunctella and its host remains elusive. In this study, 130 chemosensory genes were identified from the transcriptomes of 7 P. interpunctella tissues, and the quantitative expression levels of all 56 P. interpunctella odorant receptor genes (PintORs) were validated using real‐time quantitative polymerase chain reaction. The functional characteristics of 5 PintORs with female antennae‐biased expression were investigated using 2‐electrode voltage clamp recordings in Xenopus laevis oocytes. PintOR23 was found to be specifically tuned to acetophenone. Acetophenone could elicit a significant electrophysiological response and only attracted mated females when compared with males and virgin females. In addition, molecular docking predicted that the hydrogen bonding sites, TRP‐335 and ALA‐167, might play key roles in the binding of PintOR23 to acetophenone. Our study provides valuable insights into the olfactory mechanism of oviposition substrate detection and localization in P. interpunctella and points toward the possibility of developing eco‐friendly odorant agents to control pests of stored products. [ABSTRACT FROM AUTHOR]

Potassium iodate was employed as a mediator with concentrated sulfuric acid to electrochemically oxidize substituted secondary alcohols in a biphasic medium with platinum electrodes. Using potassium iodate as a mediator in a biphasic medium, ketones were successfully generated from secondary alcohols. 1-phenyl ethanol is electrochemically oxidized to acetophenone in a biphasic medium. With maximum selectivity and good yields, the several substituted alcohols were successfully converted to ketones. The Platinum electrode had much more electrochemical activity and electrochemical products, according to the HPLC study that followed. The product aromatic ketones were described using UV, FTIR, 1H-NMR, and 13C-NMR spectroscopy, and the percentage of product yield was calculated using HPLC. Many secondary alcohols could also be converted to the appropriate ketones at room temperature, with isolated yields ranging from 80 to 95%. During recycling, the product's purity remained intact. It appears that this concept can grow while remaining pollution-free as a result. [ABSTRACT FROM AUTHOR]

Sterically demanding organosilyl ligands support the formation of coordinatively unsaturated complexes. In this study, we found that using the ligand –Si(SiMe3)2(SiMe2tBu) affords exclusively planar three-coordinate iron bis(silyl) complexes that show good catalytic performance in the hydrosilylation of acetophenone. [ABSTRACT FROM AUTHOR]

Chiral nickel complexes containing NHC-carboxylate chelate ligands derived from the (S)-isomeric form of amino acids have been synthesised from the corresponding imidazolium salt and nickelocene. The presence of the carboxylate on the N-side arm of the heterocycle results in the competing formation of mixtures of mono- and bis-NHC complexes (i.e., [Ni(η5-Cp)(κ2-C,O-NHC)] and [Ni(κ2-C,O-NHC)2]), both of which retain the (S)-configuration of the stereogenic center and which can be separated by chromatography. Both the 18e− and 16e− complexes are found to be very stable and cannot be interconverted. The composition of the resulting mixtures depends mainly on the entity of the amino acid residue and, of more practical interest, on the reaction conditions. Thus, microwave heating and MeCN as a solvent favor the formation of the half-sandwich nickel complexes, rather than the bis-NHC compounds. Some of the [Ni(η5-Cp)(κ2-C,O-NHC)] complexes turn out to be among the best nickel catalysts for the hydrosilylative reduction of p-acetophenones described to date, although without chiral induction, in the absence of activating additives and under mild catalytic conditions. [ABSTRACT FROM AUTHOR]

The preparation of Chalcones and Pyrazoline derivatives from different aromatic ketones and substituted aldehydes is detailed. Chalcones were produced by reacting aldehydes with substituted aromatic ketones, such as acetophenones, in the Claisen-Schmidt condensation reaction. Cyclohexenone derivatives are produced when ethyl aceto aromatic ketones undergo base-catalyzed cyclo-condensation to Chalcones under microwave radiation. The synthesized compounds are characterized using spectrum techniques from 1H NMR, 13C NMR, and IR. These are examined for their antioxidant qualities as well as their antibacterial action against Staphylococcus aureus, Escherichia coli, Aspergillus niger, and Aspergillus flavus. [ABSTRACT FROM AUTHOR]

Female insects oviposit in sites suitable for the development of their offspring. The Oriental armyworm, Mythimna separata is a serious pest of various crops including wheat and prefers to oviposit on withered leaves rather than on fresh plant material, which is surprisingly different from other insects. Studies here showed that this oviposition tactic enables avoidance of wheat defence against eggs and emerged larvae. Intact plants responded to M. separata egg deposition by releasing oviposition‐induced plant volatiles including acetophenone, tetradecene and pentadecane after 24 h. Acetophenone was identified as quantitatively accounting for the attraction of the egg parasitoid wasp (Trichogramma chilonis). Leaf jasmonic acid levels significantly increased after M. separata laid eggs, and primed the plant against emerging larvae. In addition, newly emerged M. separata larvae adopted a fast crawling behaviour and starvation tolerance compared with other noctuid larvae, which enhanced the survival of larvae on the withered leaves. The elucidation of this complex and surprising plant‐insect interaction provides the first explanation for a herbivore laying eggs on withered leaves to avoid natural enemies and live‐plant defence against emerging larvae. Summary statement: Mythimna separata prefers to lay eggs on withered leaves. The result showed that this behaviour avoids plant defence against eggs and the emerged larvae. Ovipositioninduced plant volatiles, especially acetophenone, strongly attracted the egg parasitic wasps. [ABSTRACT FROM AUTHOR]

Many aroma-active compounds can be produced by means of plant-mediated reactions. Biotransformation using whole plant cells is a field of green chemistry, whose purpose is to minimize the impact on the environment in combination with the advantages of high chemo-, regio- and stereoselectivity. One such example is the asymmetric reduction of corresponding prochiral ketones to chiral alcohols. In this work, twenty-one different carrot varieties were screened as a whole-cell biocatalyst for bioreduction of acetophenone to 1-phenylethanol, an important aroma compound. The reaction catalysed by grated carrot roots was carried out in an orbital shaker, under controlled conditions (30 °C, 2.83 Hz, 24 h). The substrate and product concentrations were analysed during the reaction by gas chromatography. All tested carrot varieties showed interesting biocatalytic activity, with substrate conversion degree in the range of 55.1-85.0 %. When using Tendersweet variety, which showed the highest biocatalytic activity, the enantiomeric excess of (S)-1-phenylethanol reached 86.4 %. The influence of sugar content in carrot roots on enzyme activity was not confirmed. The results provide useful information on the application of carrot roots as a promising source for the biocatalytic conversion of acetophenone to 1-phenylethanol. [ABSTRACT FROM AUTHOR]

Objective: In this study, a series of synthetic hydroxylated (5-10) and prenylated (10-17) acetophenones, chalcones (18-20) and a flavone (21) have been synthesized and evaluated on the nematode Meloidogyne javanica. Additional phenolic compounds, including salicylic acid, isopropyl salicylate, thymol, carvacrol, cumic acid, eugenol, vanillin, and vanillic acid (22-29), were also tested. Methods: Compounds 5-21 have been synthesized by a sequence of reactions and were isolated and identified by ¹H-NMR, 13C-NMR, and HRMS. The in vitro nematicidal effects of the compounds were tested on J2 juveniles. The nematicidal activity was confirmed by their egg hatching inhibition effects, tested at the minimum lethal concentration (minimum dose to give 100% J2 mortality). Results: Compounds 5-18 have been previously reported and 19-21 are described here for the first time. The 2'-hydroxylated acetophenones (5-9) showed strong nematicidal effects, being 7-9 the most active. Salicylic (22) and cumic (26) acids were effective compounds. Compounds 7, 12, 22-26, active on M. javanica J2 juveniles, were also egg hatching inhibitors. Conclusions: A C-2/C-4 dihydroxylation or C-2/C-4/C-3 trihydroxylation of the acetophenone moiety improved the activity, while introducing a hydrophilic isoprene chain (10-17) eliminated the effect, with only one prenylated acetophenone (12) being active. Among the additional phenolic compounds (22-29), these with a carboxyl group instead of the acyl side were better nematicides. These results generate molecular leads for developing new nematicidal phenolic compounds. [ABSTRACT FROM AUTHOR]

The subject of the research was the recovery of raw materials from waste generated in the production of cable insulation and the management of aluminum sludge. It was found that 49% (w/w) acetophenone, 6.8% (w/w) α-methylstyrene, and 17.2% (w/w) cumyl alcohol can be recovered from waste with a loss on ignition of 95% and used in various industries. A gas chromatograph equipped with a mass spectrometry detector was used to identify the recovered compounds. A waste distillation process was proposed to remove the water layer and obtain a concentrated acetophenone fraction. A method of neutralizing the water fraction and distillation residues is presented. The proposed waste management method is an alternative method to the currently used thermal transformation method. In turn, aluminum sludge was used to produce aluminum sulfate, which was used in the plant's sewage treatment plant as a coagulant. The effect of this action was a reduction of 67% in the content of total iron, 60% of trivalent iron, and 32% of chemical oxygen demand. The above-mentioned examples of waste management are part of a closed-loop waste management strategy. [ABSTRACT FROM AUTHOR]

Chalcone represents a vital biosynthetic scaffold owing to its numerous therapeutic effects. The present study was intended to synthesize 17 chalcone derivatives (3a–q) by direct coupling of substituted acetophenones and benzaldehyde. The target chalcones were characterized by spectroscopic analyses followed by their in vitro antimicrobial, and antileishmanial investigations with reference to standard drugs. The majority of the chalcones displayed good to excellent biological activities. Chalcone 3q (1000 µg ml−1) exhibited the most potent antibacterial effect with its zone of inhibition values of 30, 33 and 34 mm versus Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa respectively. The results also confirmed chalcone 3q to be the most potent versus Leishmania major with the lowest IC50 value of 0.59 ± 0.12 µg ml−1. Chalcone 3i (500 µg ml−1) was noticed to be the most potent antifungal agent with its zone of inhibition being 29 mm against Candida albicans. Computational studies of chalcones 3i and 3q supported the preliminary in vivo results. The existence of the amino moiety and bromine atom on ring-A and methoxy moieties on ring-B caused better biological effects of the chalcones. In brief, the investigations reveal that chalcones (3i and 3q) can be employed as building blocks to discover novel antimicrobial agents.

Increased electricity usage over the past several decades has accelerated the need for efficient high-voltage power transmission with reliable insulating materials. Cross-linked polyethylene (XLPE) prepared via dicumyl peroxide (DCP) cross-linking has emerged as the insulator of choice for modern power cables. Although DCP cross-linking generates the desired XLPE product in high yield, other by-products are also produced. One such by-product, acetophenone, is particularly intriguing due to its aromaticity and positive electron affinity. In this work, constrained density functional theory (C-DFT) was utilized to develop an e-ReaxFF force field suitable for describing the acetophenone radical anion. Initial parameters were taken from the 2021 Akbarian e-ReaxFF force field, which was developed to describe XLPE chemistry. Then, C-DFT geometry optimizations were performed wherein an excess electron was constrained to each atom of acetophenone. The resulting C-DFT energy values for the various electronic positions were added to the e-ReaxFF training set. Next, an analogous set of structures was energy-minimized using e-ReaxFF, and equilibrium mixture compositions for the two methods were compared at multiple temperatures. Iterative fitting against C-DFT energy data was performed until satisfactory agreement was achieved. To test force field performance, molecular dynamics simulations were performed in e-ReaxFF and the resulting electronic distributions were qualitatively compared to unconstrained-DFT spin density data. By expanding our e-ReaxFF force field for XLPE, namely, adding the capability to describe acetophenone and its interactions with an excess electron, we move one step closer to a comprehensive molecular understanding of XLPE chemistry in a high-voltage power cable. [ABSTRACT FROM AUTHOR]

In the current work, new and diverse hydrazone derivatives were designed and synthesized through a facile and multistep synthetic approach. The chemical structures were elucidated by various spectroscopic techniques. In vitro bioactivity analysis demonstrated selective and potent inhibitory potential of hydrazone derivatives against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. (E)‐3‐chloro‐N′‐(1‐phenylethylidene) benzohydrazide remarkably emerged as a lead candidate exhibiting potent and selective inhibition of AChE with an IC50 value of 0.63±0.01 μM whereas (E)‐3‐chloro‐N′‐(1‐(thiophen‐2‐yl)ethylidene)benzohydrazide delivered the strong potency and selective inhibition towards monoamine oxidase A with an IC50 value of 0.89±0.04 μM. Moreover, (E)‐3‐chloro‐N′‐(1‐(4‐methylthiophen‐2‐yl)ethylidene)benzohydrazide (IC50=2.06±0.01 μM) and (E)‐3‐chloro‐N′‐(1‐(5‐chlorothiophen‐2‐yl)ethylidene)benzohydrazide (IC50=2.06±0.05 μM) were identified as lead inhibitors of monoamine oxidase B. Molecular docking studies of potent and selective inhibitors exhibited various important interactions with amino acid residues in the active pocket of both enzymes, thus strengthening our in vitro results. The kinetics analysis of the most potent compound against AChE revealed non‐competitive mode of inhibition, whereas against monoamine oxidase (A & B), the corresponding lead inhibitors exhibited mixed type of inhibition. Molecular dynamics simulations were also performed to investigate the energetically stable complex formation ability of potent compounds with the target protein. Finally, the results of in silico pharmacokinetic properties showed that the potent compounds have promising pharmacological effects that follow all the parameters of drug‐likeness and could serve as effective drug candidates for future investigations. [ABSTRACT FROM AUTHOR]

The possibility of enantioselective biotransformation of a model prochiral carbonyl compound, acetophenone, by cellular catalysts based on a number of cultures of the Fabaceae family (Phaseolus vulgaris, Lens culinaris, Cicer arietinum, Vigna radiata, and Pisum sativum) was explored. According to the rate and direction of enantioselective bioreduction, enantioselectivity, and the yield of the target products, the most promising cellular catalysts for the asymmetric bioreduction of prochiral carbonyl compounds, which enable the synthesis of target alcohols of both (S)- and (R)-configurations, were identified. [ABSTRACT FROM AUTHOR]

Enantiomerically pure alcohols are important to produce active pharmaceutical ingredients, agrochemicals and fine chemicals. Herein, we explored the substrate scope and chemo‐ and enantioselectivity of two NAD‐dependent anti‐Prelog alcohol dehydrogenases from Candida maris (Cm‐ADH) and Pichia finlandica (Pf‐ADH) in the asymmetric reduction of ketones. The ADHs were tested for the reduction of acetophenone with NADH that was recycled using a formate dehydrogenase and sodium formate. Cm‐ADH and Pf‐ADH performed best at 30 °C and at around pH 7 and pH 6, respectively. Pf‐ADH operated well at 50 mM acetophenone concentration, while Cm‐ADH was limited to 10 mM. Regarding the substrate scope, linear‐chain alkyl ketones were efficiently reduced (up to 98 % conversion), while branched and cyclic ketones gave lower conversions (up to 60 %). Aryl‐aliphatic ketones showed variable levels of conversion (<1–79 %), while α,β‐unsaturated and heteroaromatic ketones exhibited good to excellent conversions. In most of the cases, the enantiomeric excess was >99 %. Aliphatic and aryl‐aliphatic aldehydes were converted with up to >99 % conversion. A scale‐up experiment with Pf‐ADH using acetophenone as substrate led to 73 % isolated yield and >99 % ee (R). This work contributes to filling the gap in biocatalytic asymmetric synthesis of chiral alcohols by introducing two NAD‐dependent ADHs with anti‐Prelog selectivity. [ABSTRACT FROM AUTHOR]

Synthesized substituted N-acetyl-3,5-diaryl-2-pyrazolines through their chalcone intermediates and evaluated for anti-cancer activity. Chalcones were synthesized from 2,4,5-trimethoxy benzaldehyde obtained from oxidation of β-asarone ((Z)-2,4,5-trimethoxy-1-propenylbenzene) is a major active principle component found in Acorus calamus oil (70–80%) and reacting with substituted acetophenones by Claisen-Schmidt condensation. Substituted chalcones were further treated with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give directly the corresponding N-acetyl-3,5-diaryl-2-pyrazolines in 68–85% yields. Structures were confirmed by IR, GC-MS,1H NMR, and 13C NMR.These novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982, and HeLa) using MTT assay. The results reveled that among the synthesized pyrazolines, which are having electron donor groups in para position of the aryl ring, i.e. 5th position of the N-acetyl pyrazolines showed better inhibitory activity (5b, 5c, 5d, 5e, 5f, 5g, 5k, and 5j) when compared with β-asarone. The compound 3'-nitro, 4'-chloro pyrazolines (5k) showed highest IC50 values 11.67 ± 0.54, 14.17 ± 0.92, and 18.26 ± 0.98 µg/mL (P <0.05) respectively, when compared to natural precursor. [ABSTRACT FROM AUTHOR]

The introduction of iron ionic sites by metal exchange of defective homometallic nickel pyrazolate frameworks generates non‐precious, Earth‐abundant, first‐row heterometallic Fe/Ni‐pyrazolate frameworks. The Fe incorporation at the Ni nodes of the framework allows to control the hydrogen peroxide activation, minimizing its decomposition and O2 liberation, occurring at the homometallic Ni nodes. The generation of Fe−OH reactive oxygen species at the heterometallic Fe/Ni nodes is demonstrated by the higher activity in the proof‐of‐concept oxidation of 1‐phenylethanol to acetophenone in an aqueous medium. [ABSTRACT FROM AUTHOR]

Herein, we report the cobalt(II) phthalocyanine catalyzed one-pot α-alkylation reaction of ketones with primary alcohols to provide the substituted 1-phenyl-1-propanone as the desired compound. We have utilized different electron-rich and electron-deficient substituted alcohols and substituted acetophenones as the substrates for the present catalytic system. The reaction proceeds well with electron deficient and electron-rich substrates and provide good to excellent yield of products. The products are characterized and confirmed by 1 H NMR, 13C NMR, and elemental analysis techniques and the data are supported with literature values. [ABSTRACT FROM AUTHOR]

As a new sustainable catalyst and green solvent, ionic liquid has important applications in catalytic reduction. In this study, four quinuclidinol-based quaternary ammonium ionic liquids (ILs)were at first prepared using simple procedures, and then they were used as catalyst for acetophenone reduction. The main catalytic conditions were studied and screened through a comparison among the reaction results. It showed that the highest yield of 1-phenylethanol was 88.6% when [MenQu]Cl was used as a catalyst; the ideal solvent was ethanol; the amount of catalyst was 20 mol%, and the reaction temperature was 25 °C. More substrates were employed to validate the universality of the developed method using such an IL. Moreover, potential reaction mechanisms and an IL recovery method were also suggested, which laid the foundation for its further applications in the field of sustainable chemistry and cleaner industrial production. [ABSTRACT FROM AUTHOR]

A Selectfluor mediated regioselective π‐extended [3+1+1] annulation using imidazopyridines, acetophenones and DMF as carbon source has been realized. The current route compared to traditional π‐extended annulation reaction utilizes commercially available acetophenones as a cyclic partner and offers three C−C bond formations. This reaction displayed good functional group tolerance wherein DMF served as a carbon synthon. Five‐membered bridged chroman‐4‐one derivative of imidazopyridine has been achieved with 2‐hydroxy acetophenone, wherein DMF acted as a dual carbon synthon and offered four C−C and one C−O bond formation in one‐pot. [ABSTRACT FROM AUTHOR]

In the present work, organic 2-hydroxy-2-phenyl acetophenone oxime (2H2PAO) single crystal was synthesized and characterized by FT-IR, FT-Raman, UV-Vis, NMR spectra. The optimized geometrical parameters were computationally obtained at DFT/B3LYP level of theory. Harmonic vibrational frequencies were calculated and the spectral assignments have been done by potential energy distribution (PED) analysis using NCA method. The natural bond orbital (NBO), atoms in molecule (AIM) and Hirshfeld surface analysis and RDG were applied to evaluate the relative strength of hydrogen bond interactions and represent their effect on the stabilities of molecular arrangement. The chemical stability and NLO activity of title compound were evaluated by HOMO-LUMO analysis. MEP and Fukui function analysis recognizes the nucleophilic and electrophilic regions of the molecule and the chemical implication of molecule have been explained using ELF and LOL analysis. Photo-excitation of 2H2PAO has been examined to understand its light emitting behavior. Thermal stability of the grown crystal was examined by TG/DTA analysis to understand the withstanding temperature of 2H2PAO. [ABSTRACT FROM AUTHOR]

α‐Amido ketones play a crucial role in the pharmaceutical industry due to their significance. The synthesis of these compounds under metal‐free conditions has been successfully achieved. An efficient hydrogen bond‐assisted method for synthesizing α‐amido hydroxyketones was developed using I2/dimethyl sulphoxide (DMSO) to promote oxidative reactions between various acetophenones and amides. This reaction occurs under mild metal‐free conditions, resulting in the production of the corresponding α‐amido hydroxyketones in significant quantities and with good to high yields. DFT studies have revealed that the H‐bonding interaction between the carbonyl oxygen and hydroxy group leads to the formation of stable α‐amido hydroxyketones, in contrast to α‐amido dione. [ABSTRACT FROM AUTHOR]

As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminones, pyrrolo[1,2-a]pyrazines, and indolizines was evaluated on six Candida spp., including two multidrug-resistant ones. Compared to the reference drugs, most test compounds produced a more robust antifungal effect. Docking analysis suggests that the inhibition of yeast growth was probably mediated by the interaction of the compounds with the catalytic site of HMGR of the Candida species. [ABSTRACT FROM AUTHOR]

In this contribution, we propose the couple 1-Cyclohexylethanol/Acetophenone as a new biobased and bifunctional LOHC. This material shows promises for hydrogen storage by DFT modelling, while commercial catalysts were identified to carry out both hydrogenation and dehydrogenation: Ru/Al 2 O 3 was found to catalyse the complete hydrogenation of the LOHC at 115 °C in 2 h with 98% selectivity and, for the first time, Pt/C carries out the dehydrogenation at 205 °C in 36 h with total conversion but with a limited Degree of Dehydrogenation of 72%. The system was cycled three times during which up to 50% of the total hydrogen capacity was exploited, stable after 3 cycles. Kinetics experiments and DFT modelling of the reactions intermediates show that a system pairing C–O and C–C bonds is prone to degradation, due to side-reactions initiated by the O-moiety and the reversible hydrogenation of the C O bond during the dehydrogenation step. [Display omitted] • 1-Cyclohexylethanol/Acetophenone was proposed as a new biobased bifunctional LOHC. • Full hydrogenation and dehydrogenation were achieved with heterogeneous catalysts. • Energies of activation of each function was measured during the dehydrogenation. • Up to 53% of the total hydrogen capacity was exploited during the cycling. • DFT modelling rationalized the dehydrogenation pathway and degradation products. [ABSTRACT FROM AUTHOR]

[Display omitted] • Cu+ species could adsorb C O bonds and enhance C O bond hydrogenation. • Cu0 species were the main active sites for 2-propanol dehydrogenation. • Synergistic effect between CoO x acid and Cu metal sites promoted the HDO reaction. • Cu/CoO x catalysts showed universality for the HDO of biomass derivatives. The efficient hydrodeoxygenation (HDO) of biomass derivatives to yield specific products is a significant yet challenging task. In the present study, a Cu/CoO x catalyst was synthesized using a facile co-precipitation method, and subsequently used for the HDO of biomass derivatives. Under optimal reaction conditions, the conversion of 5-hydroxymethylfurfural reached 100% with a selectivity of ∼99% to 2,5-diformylfuran. In combination with the experimental results, systematic characterizations revealed that CoO x , as the acid site, tended to adsorb C O bonds, and the metal sites of Cu+ were inclined to adsorb C O bonds and enhance C O bond hydrogenation. Meanwhile, Cu0 was the main active site for 2-propanol dehydrogenation. The excellent catalytic performance could be attributed to the synergistic effects of Cu and CoO x. Further, by optimizing the ratio of Cu to CoO x , the Cu/CoO x catalysts exhibited notable performance in HDO of acetophenone, levulinic acid, and furfural, which verified the universality of the catalysts in the HDO of biomass derivatives. [ABSTRACT FROM AUTHOR]

Acetophenone is a reagent used in various consumer products, including fragrance chemicals in toys and childcare products. Contact with acetophenone-containing materials can harm human health, and therefore acetophenone migration levels should be controlled. A new procedure for the quantification of acetophenone migrated to air and water from toys and school supplies using solid-phase microextraction and gas chromatography with mass spectrometric detection is proposed. The optimal combination of acetophenone response and its relative standard deviations was achieved for air samples after 10-min extraction at 25°C and for water samples after the addition of 3.5 g of salt, agitation/preincubation at 500 rpm for 5 min at 60°C, and 20-min extraction by polydimethylsiloxane/divinylbenzene fiber. The developed procedure provided linear calibration with R2 > 0.996 at 1–50 µg/m3 in air and 1–20 µg/L in water, and low limits of detection and quantification of acetophenone in the air (0.01, 0.04 µg/m3) and water (0.01, 0.03 µg/L). Spike recoveries of acetophenone were 109–116% for air and 90–111% for water. Acetophenone concentrations migrated from toys and school supplies into the air ranged from 0.6 to 1.5 µg/m3, except for eraser type II (9.7 µg/m3) which exceeded the maximum permissible concentration by 3.2 times. Acetophenone concentrations migrated to water were 1.3–3.5 µg/L. [ABSTRACT FROM AUTHOR]

A series of (E)-1-(3/4-{[(E)-(2-chloroquinolin-3-yl)methylidene]amino}phenyl)ethan-1-one oximes 3a–3j have been designed and synthesized by the condensation of 2-chloroquinoline-3-carbaldehydes and (E)-1-(3/4-aminophenyl)ethan-1-one oximes using glacial acetic acid as a catalyst. The structures of the newly synthesized compounds were characterized by 1H and 13C NMR, FT-IR, and mass spectra. All compounds 3a–3j were assessed for their drug likeness and ADMET properties using computational analysis. They showed optimal drug scores and negligible toxicities and satisfied Lipinskiʼs rule of five. Compounds 3f, 3h, and 3i exhibited significant antimicrobial activity against Gram-positive (S. aureus, B. subtilis) and Gram-negative bacteria (S. Typhi, P. aeruginosa) and fungi (A. niger, A. flavus), whereas compounds 3g–3j showed antimyco-bacterial activity against Mycobacterium tuberculosis H37Rv strain with MIC in the range of 1.6 to 100 µg/mL. [ABSTRACT FROM AUTHOR]

Thiazolidinediones (TZDs) are the vital component of a number of pharmaceuticals and biologically active compounds. Owing to the diversified pharmaceutical applications of TZD derivatives, we conceived a new synthetic approach for the preparation of a series of spiro-thiazolidinediones by the reaction of synthesized TZDs with thioglycolic acid. Melting point and thin-layer chromatography ascertained the purity of the synthesized compounds. Elemental analysis, FTIR, 1H and 13C NMR spectral studies have been used for the characterization of the synthesized compounds. The synthesized chalcones, thiazine, TZDs, and spiro-thiazolidinediones are in accordance with the standard values of different spectral techniques. The appearance of a sharp singlet of two protons of CH2 at 2.5 – 3.0 ppm in 1H NMR of spiro-thiazolidinediones, which was absent in TZDs, suggests the formation of a spiro ring. All the novel compounds were screened for their antimicrobial activity on Gram-negative (P. aeruginosa, E. coli) and Gram-positive (B. subtilis, S. aureus) bacteria. The final synthesized compounds exhibited excellent to good responses against the tested microbes. The change of the substituent and its position plays a significant role in the activity of the synthesized spiro-thiazolidinediones. [ABSTRACT FROM AUTHOR]

In this study, we aimed to establish an efficient method for synthesizing two new series of arene-linked pyrazolo[1,5-a]pyrimidines. This was achieved by reacting 1H-pyrazole-3,5-diamines with the respective acetophenones and benzaldehydes in a 1:1:1 ratio. To optimize this three-component reaction, various bases, and solvents were investigated. Use of two equivalents of KOH in ethanol at reflux for 4--6 h resulted in 89%--96% yields of the desired products. Structure of new products was elucidated by considering their elemental and spectral data. [ABSTRACT FROM AUTHOR]

A base‐free and efficient tandem one‐pot α‐ketoamide bond formation via tert‐butyl hydroperoxide (TBHP) mediated oxidative coupling of α‐hydroxy acetophenones with primary and secondary amines under Ag(I)‐N‐Heterocyclic carbene (Ag(I)−NHC) catalysis in water was developed herein for the first time. [ABSTRACT FROM AUTHOR]