Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Fershtat, Leonid L.; Teslenko F.

doi:10.1055/a-1529-7678

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Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Synthesis. 2021. Vol. 53. No. 20. P. 3673–3682.

Fershtat, Leonid L., Teslenko F.

Five-membered heterocyclic N-oxides attract special attention due to their significant potential applications in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are in constant demand. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are summarized. The main routes involving transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. The transformations of these hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

Research target: Chemistry

Language: English

DOI

Keywords: nitrogen heterocycles cycloaddition 1,2,5-oxadiazoles 1,2,3-triazoles C-H functionalization isoxazolines ring cleavage

Surface-sulfonated Al₂O₃, CeO₂, and TiO₂ as functional fillers for Nafion-type gel polymer electrolytes for lithium metal batteries

Voropaeva D., S. Novikova, I. Stenina et al., Solid State Ionics 2026 Vol. 445 Article 117288

Composite gel polymer electrolytes based on a perfluorinated sulfonic acid cation-exchange MF-4SC membrane containing surface-sulfonated nanoparticles of aluminum oxide, cerium (IV) oxide, and titanium oxide (sAl2O3, sCeO2, and sTiO2, respectively) were prepared by casting from a dispersion in N,N-dimethylformamide and plasticized with a 1,3-dioxolane/1,2-dimethoxyethane mixture. The influence of the filler nature on ionic conductivity, solvent uptake, activation energy, lithium ...

Added: July 30, 2026

Long-range machine-learning potentials with environment-dependent charges enable predicting LO-TO splitting and dielectric constants

Korogod D., Shapeev A., Ivan S. Novikov, Physical Review B: Condensed Matter and Materials Physics 2026 Vol. 114 No. 2 Article 024104

We present two models with explicit long-range electrostatics in the form of Coulomb interactions. Both models include point charges depending on their local atomic environments, and the second model also conserves a total charge of an atomic system. We combine the proposed long-range models with the local moment tensor potential (MTP) and demonstrate that they ...

Added: July 22, 2026

A Way to Create Mn-Containing GdFe3(BO3)4 and the Dopant Effect on Its Magnetic Properties

Moshkina E., Molokeev M., Zolotov A. et al., Journal of Alloys and Compounds 2026 Vol. 1077 Article 189412

A wide series of substitutions in a subsystem of small radii cations M = Al, Cr, Fe, Ga, Sc is possible in rare-earth borates ReM3(BO3)4 with the huntite structure. However, the existence of these compounds where M = Mn still raises doubts. The study presents a synthetic approach developed in the framework of the flux method allowing for the required ...

Added: June 29, 2026

Incorporating Scientific Knowledge into Neural Network Density Functionals

Schneider M., Zaripov D., Dokin R. et al., Journal of Chemical Theory and Computation 2026 Vol. 22 No. 9 P. 4405–4414

Density functional theory (DFT) is the workhorse of modern reactions and materials modeling. While the exact functional remains unknown, many approximations to it have been constructed either by hand-crafting functional forms to satisfy exact constraints or by machine learning. In this work, we show how both of these approaches can be fused to build both ...

Added: June 26, 2026

Annulation of aliphatic nitro compounds with β-styryl sulfonium salts toward the synthesis of isoxazoline N-oxides

Ushakov P., Organic and Biomolecular Chemistry 2026 Vol. 24 P. 2725–2731

Vinyl sulfonium salts have proved to be convenient building blocks in modern organic synthesis due to the wide variety of their reactivities. In this study, we expand the spectrum of possible transformations using the annulation reaction with aliphatic nitro compounds as bis-nucleophilic species. The resulting isoxazoline N-oxides, which exhibit a previously difficult-to-obtain substitution pattern, turned out ...

Added: June 25, 2026

Recent advances in the application of the isoxazoline route to aldols in the synthesis of natural products

Ushakov P., Natural Product Reports 2025 Vol. 42 P. 876–910

The cycloaddition of nitrile oxides with olefins (NOC), followed by reductive cleavage of the resulting isoxazolines, has been widely recognised as a convenient and powerful synthetic strategy for constructing the aldol motif in natural product synthesis. Different modes of NOC (intermolecular, fused and bridged intramolecular) enable the synthesis of diverse isoxazoline products, which can be ...

Added: June 25, 2026

Electrodeposition and electrochromic properties of hydrated mixed oxides MoxW1-xO3·2H2O films

Laurinavichyute V., Levin E. E., Mironkova A. A. et al., Surfaces and Interfaces 2026 Vol. 81 Article 108389

In this work we characterize mixed Mo-W acidic deposition solutions with Mo content ranging from 0 to 100 mol.% by Raman and UV–Vis spectroscopy. The obtained distribution diagram of mixed isopolyanions allows one to explain the observed change in film deposition rate with increase in Mo content. It was found that the initial decrease in ...

Added: June 24, 2026

Impact of heat treatment on microstructure and mechanical properties of additively manufactured aluminum bronze

Filippova A. V., Yurchenko N. Y., Smirnov S. A. et al., Journal of Alloys and Compounds 2026 No. 1074 Article 189162

This study investigates the effects of post-processing heat treatment at 300–500 °C on the microstructure, hardness, and tensile properties of laser powder bed fusion (PBF-LB) processed Al-bronze processed with energy densities (ED) in the range of 125–938 J/mm3. In the as-printed state, sharp needle-like α + β′ laths form at lower ED whereas with increasing ED, the β′ ...

Added: June 12, 2026

DFT-guided charge-state engineering of gold clusters for levodopa recognition: fundamental principles for drug delivery applications

Obijiofor O., Novikov A., New Journal of Chemistry 2026 Vol. 50 No. 23 P. 9749–9768

Rational design of gold-based nanocarriers for neurotherapeutics requires atomic-scale understanding of drug-material interactions. Density functional theory calculations were performed to investigate levodopa (L-DOPA) adsorption on small gold clusters (Au2–Au4) with cationic, neutral, and anionic charges, with additional validation on a larger Au10 cluster using multiple low-energy isomers. Binding free energies (ΔGbind), charge transfer, and electronic descriptors ...

Added: June 3, 2026

Facile and Green Approach to Synthesize Biomass-Derived Zero-/Two-Dimensional Carbon Dots/g-C3N4 Heterojunction for Efficient Photocatalytic and Photoelectrocatalytic Applications

Das A., Saikia J., Maji N. et al., ChemNanoMat 2026 Vol. 12 No. 5 Article e202500733

Developing efficient photoactive materials from bio-derived resources is vital yet challenging for achieving effective water splitting performance. In this work, nano carbon dots (CDs) of zero-dimensional (0D) were synthesized from papaya peel through a simple and eco-friendly process and subsequently anchored onto the two-dimensional (2D) layered structure of graphitic carbon nitride (g-C3N4, GCN) at various ...

Added: June 2, 2026

Optimal Design of Copper-Doped ZnO Heterostructures for Photocatalytic and Photoeletrochemical Performance: A Combined Experimental and DFT Study

Wary R. R., Mahato B., Sharma N. et al., The Journal of Physical Chemistry Letters 2026 Vol. 17 No. 17 P. 5099–5107

Development of heterojunction materials is an efficient approach for enhancing photocatalytic and photoelectrochemical processes. We develop a ZnO/CuO heterojunction via Cu doping into a ZnO matrix. Structural characterization confirmed that Cu was effectively incorporated into ZnO without any structural changes. The improved optical properties and reduced charge carrier recombination of the doped samples were confirmed ...

Added: June 2, 2026

Synergistic Multimetal Effects in a High-Entropy Perovskite Oxide Anchored on Reduced Graphene Oxide for Accelerated Water Oxidation

Ostovari Moghaddam A., Mehrabi-Kalajahi S., Hossein Vasigh S. A. et al., The Journal of Physical Chemistry Letters 2026 Vol. 17 No. 13 P. 3978–3985

Water electrolysis is a key technology for sustainable energy conversion and hydrogen generation. Recently, high-entropy oxides (HEOs) have emerged as promising materials because they allow tuning of structural, electronic, and catalytic properties in multifunctional systems. Here, we report the synthesis of a multicomponent La(FeCoCuTiNiMnMgSnZn)O3 perovskite, and its hybridization with reduced graphene oxide (rGO) to form a ...

Added: June 1, 2026

Band Gap Renormalization Drives Ultrafast Charge Separation and Slow Recombination in Covalently Functionalized Carbon Nanotubes: Nonadiabatic Molecular Dynamics Simulation

Chowdhury U., Mondal S., Dey S. et al., Journal of the american chemical society 2026 Vol. 148 No. 23 P. 24538–24550

Covalent functionalization offers a versatile platform to engineer carbon nanotube properties for optoelectronics applications. We demonstrate by atomistic quantum dynamics simulation that covalent functionalization can renormalize the CNT band gap, split the degenerate CNT band edge states, and strongly influence charge carrier separation and recombination dynamics. Open-ring CNT functionalization (O-CNT) largely retains the π-conjugation, whereas ...

Added: June 1, 2026

An IQA/QTAIM Approach to the Chalcogen Bond

Jiménez-Grávalos F., Alexander S. Novikov, Pendás Á. M., Communications in Computational Chemistry 2026 Vol. 8 No. 2 P. 203–210

Chalcogen bonds (ChBs) are often interpreted as 𝜎-hole driven electrostatic interactions between a chalcogen atom and a Lewis base, yet their covalent character remains under active discussion. Here, we present a real-space, reference-free study of prototypical X2Ch···X– complexes (X = F, Cl; Ch = O, S) using the Interacting Quantum Atoms (IQA) energy decomposition within ...

Added: May 27, 2026

Singlet oxygen-mediated oxidation of sulfides with palladium(II) porphyrinates: The effect of partly conjugated peripheral substituents

Uskov F., Korobkov S., Birin K. P. et al., Journal of Photochemistry and Photobiology A: Chemistry 2026 Vol. 474 Article 116936

Oxidation of sulfides by singlet oxygen has been extensively studied, yet the structure-photoactivity relationship of these photosensitizers remains underinvestigated. In the present work the photocatalytic performance of a set of functionalized palladium(II) porphyrinates was comprehensively investigated in the photocatalytic oxidation of sulfides to reveal mutual influence of structural peculiarities onto the photosensitizing properties. The photophysical ...

Added: May 27, 2026

Synthesis of Zwitterionic conjugates of cobalt Bis(dicarbollide) with BODIPY and their Photophysical properties and biological studies

Mezentsev I., Dudarova N., Druzina A. et al., Journal of Photochemistry and Photobiology A: Chemistry 2026 Vol. 479 Article 117316

Novel cobalt bis(dicarbollide) based terminal alkynes with charge-compensated group in a spacer were synthesized by the nucleophilic ring-opening reactions of cyclic oxonium derivatives of cobalt bis(dicarbollide) with N,N-dimethylbut-3-yn-1-amine. A series of zwitterionic conjugates of cobalt bis(dicarbollide) with BODIPY were synthesized using the copper(I)-catalyzed azide-alkyne cycloaddition reaction. The absorption-emission spectra of the synthesized fluorescent conjugates of cobalt ...

Added: May 27, 2026

Revealing Structure-Reporting Patterns of Pyruvylation Effects on 13C NMR Chemical Shifts in Natural Saccharides

Toukach P., Smirnova N. S., Zdorovenko E. L. et al., Analytical Chemistry 2026 Vol. 98 No. 15 P. 10988–10996

Pyruvylation is one of the immunochemically relevant modifications of O-antigens in bacterial and fungal cells. Therefore, fast and relatively simple analytical methods for identifying this modification are highly demanded. 13C NMR spectroscopy is the best candidate for this purpose, but its successful application requires using reference structures and reliable databases. In this work, we collected ...

Added: May 25, 2026

Sodium Hypophosphite Assisted Ruthenium Catalyzed Reductive Amination under Mild Conditions

Зверева О., Kliuev F., Lebedeva N. et al., Organic Letters 2025 Vol. 27 No. 50 P. 13711–13716

Added: May 23, 2026

TBAT as “Multitool” Catalyst for Polysiloxane Synthesis, Modification, and Recycling

Mikhail A. Losev, Andrey S. Kozlov, Afanasyev O. et al., ACS Catalysis 2026 Vol. 16 No. 10 P. 9380–9386

A convenient, stable, and non-toxic substance, tetrabutylammonium difluorotriphenylsilicate (TBAT), can be used as an organocatalyst in all stages of polymer lifetime: synthesis, modification, and recycling. The fluorine-containing initiator showed high activity in the polymerization of siloxanes compared to classic organocatalytic systems. Using kinetically controlled ROP, a high-molecular-weight PDMS (Mn up to 820 𝑘𝑔/𝑚𝑜𝑙) was prepared at room ...

Added: May 22, 2026

Reductive coupling of nitroarenes with carboxylic acids – a direct route to amide synthesis

Лосев М. А., Козлов А. С., Kliuev F. et al., Organic and Biomolecular Chemistry 2023 Vol. 21 No. 42 P. 8477–8481

A simple and atom-efficient way to prepare amides directly from carboxylic acids and nitroarenes was developed. Carbon monoxide as a sole reducing agent provides the ultimate selectivity of the protocol. A straightforward and selective way for the preparation of amides from nitroarenes and carboxylic acids using carbon monoxide as a reductant was developed. This protocol ...

Added: May 22, 2026

Dataset of solubility values for organic compounds in binary mixtures of solvents at various temperatures

Malikov D., Krasnov L., Kiseleva M. et al., Scientific data 2026 Vol. 13 Article 727

Solubility is a crucial property of organic compounds, impacting their potential applications in synthetic chemistry, materials science and drug design. Moreover, in technological processes mixtures of solvents are often utilized, making the solubility assessment more complicated. Predicting solubility values in mixtures of solvents from a molecular structure can help to address this issue, although a ...

Added: May 19, 2026

Insight into the structural and energetic features of substituted triazolofurazans

Sofya P. Balabanova, Alexey A. Voronin, Churakov A. et al., CrystEngComm 2024 Vol. 25 P. 3349–3362

A comparative study of experimentally established structures, stability and energetic performance of ammonium and hydrazinium salts of 4H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole (triazolofurazan, TF) as well as its N-oxide and N-nitroimide was performed. The aim of this study was to reveal the structure–property relationships of heterocyclic systems by the example of triazolofurazan derivatives. It was shown that the introduction of N-oxide oxygen ...

Added: March 7, 2025

A new conjugated tripoid N4 system containing furazan and triazolofurazan cores linked by a nitrogen bridge

Балабанова С. П., Voronin A., Churakov A. et al., Mendeleev Communications 2024 Vol. 34 No. 6 P. 862–864

Two thermostable representatives of methyl-substituted triazolofurazan derivatives with zwitterionic N+N– bonds were obtained via the thermal cyclization of N,N’-bis(azidofurazanyl)-N-methyltriazene. 5-(N-Azidofurazanyl-N-methylamino)triazolofurazan was the product of known intramolecular reaction of neighboring azido and azo groups. Its isomer with methyl group in the triazolofurazan core was formed in the course of new cyclization of azido and triazene groups representing an original NN ...

Added: March 7, 2025

Synthetic Strategies for C‐Amino 1,2,3‐Triazoles and Their Oxides: A Review

Sofya P. Balabanova, Alexey A. Voronin, Чураков А. М. et al., Journal of Heterocyclic Chemistry 2024 Vol. 61 No. 12 P. 2106–2125

The review is devoted to synthetic methods for the preparation of C-amino 1,2,3-triazoles and their oxides being important precursors in the development of energetic compounds as well as in biological, medicinal, organic, bio-organic, polymer, and material chemistry. This research mainly covers papers published after year 1986. ...

Added: March 7, 2025