Current Organocatalysis - Volume 12, Issue 1, 2025

In recent years, the use of nanomaterials as heterogeneous catalysts has attracted much attention in organic reactions.

A magnetically separable mixed metal oxide, Manganese Zinc Iron Oxide (Mn2O3/Fe3O4/ZnO) nanoparticles as nanocatalyst (Mmo@NCt) were synthesized using ultrasonic wave methods in the presence of polyethylene glycol as surfactant. In the second part of the present study, a practical procedure for the one-pot ternary condensation of aromatic aldehydes, β-naphthol, and urea in short reaction time for the synthesis of pharmaceutically interesting naphtho[1,2-e][1,3]oxazine derivatives using Mmo@NCt as an efficient, cost-effective and recyclable nanocatalyst under green conditions has been developed.

The analysis of phase purity, magnetic structure, size, and morphology of the as-synthesized nanocatalyst was characterized by X-ray diffraction, VSM, SEM, and EDX techniques. The results of SEM imaging showed that all compounds have a spherical morphological structure with a mean diameter of 16.50 ± 3.94 nm. The structure of the products was confirmed by FT-IR, 1H-NMR spectroscopy, and melting point.

This project was designed and performed with the use of magnetic nanocatalysts as a suitable method with high efficiency a shorter time for the synthesis of naphthoxazinones heterocyclic compounds due to the medicinal importance of water as a green solvent.

This study investigates the synthesis of dihydropyrimidinethiones using a multifunctional deep eutectic solvent (DES) composed of Choline chloride (ChCl) and ammonium thiocyanate. This DES serves as a catalyst, solvent, and reagent, providing a simple, high-yielding, and environmentally friendly method for dihydropyrimidinethione synthesis. The use of DES in this capacity offers several advantages, including reduced environmental impact, high efficiency, and ease of use, highlighting its potential as a sustainable alternative in organic synthesis.

The objective of this study is to investigate the application of a deep eutectic solvent (DES) composed of ChCl and ammonium thiocyanate as a catalytic solvent and reagent system for synthesizing dihydropyrimidinethiones. The aim is to simplify the reaction setup, improve yields, and enhance the green metrics of the process.

ChCl and ammonium thiocyanate were combined to form a DES catalyst-solvent system. Dihydropyrimidinethiones were synthesized in one-pot reactions at ambient temperature. Green metrics and DES recovery were evaluated. Comparative analysis with traditional methods was conducted.

The DES efficiently catalyzed dihydropyrimidinethione synthesis with high yields. Simplified reaction setup, safe solvent properties, and favorable green metrics. DES was recoverable and reusable, outperforming traditional methods in efficiency and eco-friendliness.

The ChCl and ammonium thiocyanate DES demonstrated remarkable efficiency and eco-friendliness in dihydropyrimidinethione synthesis. The toxicity-free, multifunctional roles of the DES, serving as a catalyst, solvent, and reagent, highlight its novelty and potential as a sustainable alternative in organic chemistry. This study simplifies the synthesis process and improves yields and green metrics, showcasing the DES as a promising candidate for future research and industrial applications.

Synthesis of NiO nanoparticles using environmentally friendly Pongamia pinnata seeds as a source of fuel was demonstrated using a solution combustion approach.

The protocol for the synthesis of NiO NPs is simple and efficient. NiO NPs were utilized as the catalyst for the synthesis of N-protected aminoalkyl sulfides from N-protected alkyl thiols and bromo esters of amino acids.

The NiO NPs were characterized using XRD, SEM, and EDX techniques. N-protected aminoalkyl sulfides were characterized by HRMS, ¹H, and ¹³C NMR techniques and were evaluated for their in vitro antifungal activities, against A. Niger using Fluconazole as a standard.

The current study presents an effective approach for synthesizing a new class of sulfides from N-protected aminoalkyl thiols and bromomethyl esters in the presence of nano NiO as a catalyst.

Phosphine-catalyzed asymmetric allylic alkylation of isoxazol-5(4H)-ones with achiral Morita-Baylis-Hillman (MBH) carbonates has been developed. A series of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were obtained in 55-96% yield with 75-90% ee. Gram-scale reaction and further transformation of allylation products were conducted to demonstrate the synthetic practicability.

Under Ar atmosphere, the mixture of isoxazol-5-one 1 (0.1 mmol), MBH carbonate 2 (0.12 mmol, 1.2 equiv), catalyst P5 (10 mol%), and 4Å MS (10 mg) in toluene (1 mL) was stirred at 0°C for 24 h. The solvent was removed under vacuum, and the residue was purified by flash chromatography (petroleum ether/ethyl acetate = 3/1) to provide product 3.

We developed an efficient and enantioselective allylic alkylation of isoxazol-5(4H)-ones with achiral MBH carbonates in the presence of chiral phosphine catalyst. A broad range of isoxazol-5(4H)-ones bearing all-carbon quaternary stereocenters were prepared with high efficiency and enantioselectivity. Importantly, the organocatalytic δ-stereocontrol of MBH carbonates was achieved via the synthetic strategy.

Heterocyclic compounds with O, N, and/or S atoms are highly valuable in drug discovery and development. Their pyrazole moieties find applications in various fields, such as herbicides, corrosion inhibitors, electron transport materials, polymers, and luminescent materials. Consequently, there is a pressing need in medicinal chemistry to develop new antibacterial agents to enhance therapeutic efficacy and safety.

A newer biologically active 1-(4-substitutedphenyl)-5-chloro-3-methyl-1Hpyrazole-4-carboxylic acid analogue was synthesized by the para-substituted phenylhydrazine. All the synthesized compounds were characterized by NMR, mass spectral, and IR spectrum examinations, as well as C, H, and N analyses. The synthesized compounds were screened for antibacterial and antifungal activities. Furthermore, a molecular docking study was performed to elucidate the binding modes of synthesized ligands in the active pockets of DNA gyrase and CYP51 (PDB IDs: 4uro and 5tz1, respectively) for exhibiting the binding modes and predicting the mechanism of action of synthesized ligands.

Five compounds (2Rb, 2Re, 2Rg, 2Rh, and 2Ri) demonstrated significant antibacterial action against gram-positive B. subtilis and gram-negative E. coli and antifungal activity against C. albicans and A. niger compared to the standard drugs cefixime and ketoconazole. Furthermore, molecular docking was employed to reveal how the newly synthesized ligands bind within the active pockets. It was found that compound 2Rb demonstrated significant antibacterial activity, and compound 2Rg had good antifungal activity.

The current study highlights the unique structural characteristics and significant biological activity of the synthesized compounds. In the pursuit of novel antibacterial and antifungal molecules, these compounds could prove beneficial to society.

This research article describes the production, quantification, and purification of Belinostat from 3-nitrobenzaldehyde as the starting material. A cascade-step process produces higher yields when compared to all previous existing methodologies.

The procedure involved the following: Horner–Wadsworth–Emmons (HWE) reaction of aromatic aldehydes with triethylphosphonoacetate in the presence of potassium carbonate, reduction of the nitro group to the amino group, sulfochlorination by thionyl chloride, aniline-mediated sulfonamidation, and hydroxylamine amidation as the last step.

The prepared solid Belinostat was purified, and an acceptable yield of 56-60% was obtained.

The approach has several key benefits, including low-cost beginning materials, straightforward techniques, safer and more reliable results, and substantial environmental advantages.

The catalysts were fabricated via chemical method. the catalysts exhibit large surface area, excellent porosity, excellent catalytic activity, and insolubility and can be easily separable from the reaction mixture.

The sequential use of MIL-100(Fe) MOF and MnO2 nanosheets could showcase 92% degradation of amoxicillin within 1.5 hours under ambient conditions without any significant residual bi-product as confirmed by LCMS studies.

Impressively, the antimicrobial susceptibility of degraded residue is lessened by 33% as compared to pure amoxicillin.

Biotransformation is a powerful process for producing steroid compounds, and fungi are commonly regarded as effective biological agents for this purpose. They facilitate reactions that are difficult to perform via conventional chemical methods.

In the current study, the ability of Penicillium aculeatum to biotransform progesterone was studied.

Forty-eight hours after the incubation of active P. aculeatum with substrate (progesterone), the reaction medium was extracted and chromatography methods isolated metabolites. The chemical structures of the products were characterized by various spectroscopic techniques.

Two main hydroxylated products, 14α-hydroxyprogesterone, and 7α,14α-dihydroxyprogesterone, were finally identified.

P. aculeatum may be considered a functional biocatalyst for some biotransformation processes.

Solifenacin succinate is an active pharmaceutical drug molecule that is extremely effective in treating overactive bladder symptoms, such as urine incontinence, urgency, and frequent urination. The free base is yellow oil, and the salt solifenacin succinate forms yellowish crystals that are extremely stable and effective. Solifenacin is a very active antagonist due to its potent muscarinic M3 receptor antagonist characteristics. Furthermore, solifenacin is effective in the treatment of bowel syndrome (IBS) by blocking M3 receptors and a broad spectrum of bowel dysfunction.

The objective of this study was to develop a practical and highly efficient scalable synthesis of enantiomerically pure solifenacin as an antimuscarinic agent.

In this work, the Zn(OTf)2 catalyst was used to develop a novel, environmentally benign, high-yielding, and robust protocol for the synthesis of enantiomerically pure solifenacin succinate.

The synthesis of enantiomerically pure solifenacin succinate was achieved in seven steps using commercially available phenylethylamine and benzoyl chloride as the starting materials. We carried out the reaction optimization by treatment of (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carbonyl chloride and (R)-(-)-3-Quinuclidinolin in the presence of Zn(OTf)2 catalyst. Furthermore, the solifenacin-free base was treated with succinic acid to afford its corresponding salt. The highlight of this protocol is the use of 20 mol% Zn(OTf)2catalyst for the first time. The readily available starting materials, robustness, easy operation, high yield, and low cost make the approach more attractive and highly applicable.

In summary, we developed a novel Zn(OTf)2-catalysed environmentally benign, high-yielding, and robust protocol for the synthesis of enantiomerically pure solifenacin succinate. The proposed strategy is highly cost-effective and avoids the use of hazardous and unsafe sensitive, strong bases as well as tedious work-up procedures. Effective synthesis was achieved using readily available starting materials and reagents. Thus, the protocol is highly efficient, compatible, and commercially viable for the synthesis of important solifenacin products.