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Organics

Organics is an international, peer-reviewed, open access journal on organic chemistry published quarterly online by MDPI.

All Articles (198)

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1,3-Dipolar cycloaddition reactions of nitrile imines are a powerful tool for the construction of spirocyclic frameworks, yet controlling chemoselectivity remains challenging when dipolarophiles contain multiple reactive sites. In this study, we investigated the cycloaddition of nitrile imines with 5-arylmethylene-2-methylthiohydantoins, which possess both exocyclic C=C and endocyclic C=N bonds. Nitrile imines were generated from hydrazonoyl chlorides under basic conditions and reacted with the thiohydantoin substrates under optimized reaction conditions. The cycloaddition proceeded smoothly, affording spiro-fused thiohydantoin–pyrazoline derivatives. In all cases, the reaction occurred selectively at the exocyclic C=C bond, while the C=N bond remained unreactive even in the presence of excess dipole. This chemoselectivity is attributed to the greater steric accessibility of the exocyclic double bond. These results clarify key factors governing nitrile imine chemoselectivity and provide a reliable approach to structurally complex spirocyclic thiohydantoin derivatives.

3 February 2026

Optimization of cycloaddition reaction conditions of hydrazonoyl chloride 2a with 5-arylmethylene-2-methylthiohydantoin 5a. Unless otherwise noted, reactions were carried out at room temperature under an argon atmosphere using 5-arylmethylene-2-methylthiohydantoin 5a (0.071 mmol, 0.026 g) and the corresponding hydrazonoyl chloride 2a in 3.5 mL of solvent for 24 h. a Product yields were determined by 1H NMR analysis of the crude reaction mixtures using CH2Br2 as an internal standard. b Initially, 1.1 equiv. of hydrazonoyl chloride 2a and 2.2 equiv of Et3N were added and the mixture was stirred for 6 h; a second portion of 2a (1.1 equiv) and Et3N (2.2 equiv) was then introduced, followed by stirring for an additional 6 h.

A sustainable hybrid material, CuO/Cu2O, was synthesized using an aqueous extract of Curcuma longa L. as a reducing and stabilizing agent. The material was characterized by UV-Vis spectroscopy, FTIR, XRD, SEM, EDX, and TEM. XRD analysis revealed peaks corresponding to CuO and Cu2O phases with crystallite sizes of 15.88 nm and 16.71 nm, respectively. TEM images showed nearly spherical particles with some agglomeration and an average particle diameter of 8.17 nm. The hybrid material exhibited catalytic activity toward the synthesis of 1,2,3-triazoles in water, under low catalyst loading and mild reaction conditions. This work highlights the potential of Curcuma longa-mediated synthesis as a low-cost, eco-friendly alternative for producing efficient catalysts, contributing to the advancement of green chemistry and sustainable nanomaterial applications in organic synthesis.

23 January 2026

UV–visible spectrum of aqueous extract of Curcuma longa L. and non-calcined CuO/Cu2O NPs (a); absorption spectrum of CuO/Cu2O NPs after calcination (b).

Commercially available resorufin was shown to function as an organic photocatalyst for visible-light-induced aqueous radical polymerization under low-irradiance illumination. Polymers with narrow molecular weight distributions and high monomer conversions were successfully synthesized from acrylate and acrylamide monomers. The photopolymerization catalyzed by resorufin was consistent with a reductive quenching mechanism. Good temporal control of the reaction was achieved by toggling visible light irradiation.

15 January 2026

Abbreviations and chemical structures of (a) the electron donor, (b) the resorufin, (c) the initiator, and (d–g) the monomers used in this study.

The development of a metalloenzyme-like catalytic system for the efficient oxidation of olefins under a dioxygen (O2) atmosphere at room temperature is of significant interest in the field of catalysis. Herein, we present a highly active and selective aerobic epoxidation of olefins using metalloenzyme-like catalysts based on a non-heme ligand, tris(2-pyridylmethyl)amine (TPA). Notably, manganese chloride complexed with TPA (Mn(TPA)Cl2) demonstrated excellent activity for the epoxidation of trans-stilbene using O2 as the oxidant in the presence of a co-reductant at 30 °C. A quantitative conversion of 99% and high yield of 98%, as determined by gas chromatography using an external standard method, were achieved under optimum reaction conditions. Furthermore, Mn(TPA)Cl2 exhibited a good substrate tolerance to styrene derivatives with electron-withdrawing or electron-donating groups, cyclic olefins with different substituents and substitution degrees, as well as long-chain olefins. Coupled with a high turnover frequency (TOF) of up to 30,720 h−1, these results underscore the potential of Mn(TPA)Cl2 as a promising metalloenzyme-like catalytic platform for the aerobic synthesis of diverse epoxides from olefins under ambient conditions.

7 January 2026

Effect of various aldehydes on the aerobic epoxidation of trans-stilbene. Reaction conditions: trans-Stilbene (1.0 mmol), isobutyraldehyde (5.0 mmol), Mn(TPA)Cl2 (0.005 mol%), O2 bubbling (10 mL min−1), CH2Cl2 (5 mL), 30 °C.

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Organics - ISSN 2673-401X