Route to 1,2,4-and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol

I. Ananyev; Тесленко Ф. Е.; Чураков А.; Ларин А.; Ферштат Л. Л.; Махова Н. Н.

doi:10.1016/j.tetlet.2020.151678

Publications

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Route to 1,2,4-and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol

Tetrahedron Letters. 2020. Vol. 61. No. 13. P. 151678-1–151678-5.

Ananyev I., Тесленко Ф. Е., Чураков А., Ларин А., Ферштат Л. Л., Махова Н. Н.

A novel one-pot approach for the synthesis of 1,2,4- and 1,2,5-oxadiazole ring assemblies has been developed. The synthetic strategy involves the condensation of furoxanyl amidoximes with aldehydes and subsequent iodine-mediated oxidation of the intermediate 1,2,4-oxadiazolines. The analogous reaction of 4-aminofuroxanyl-3-carboxamidoxime results not only in formation of the 1,2,4-oxadiazole subunit, but also rearrangement of the furoxan ring to the furazan one, which is the first example of a Lewis acid-promoted rearrangement in a furoxan series

Research target: Chemistry

Keywords: condensation nitrogen heterocycles конденсация Oxadiazoles Synthetic methods оксадиазолы азот-содержащие гетероциклы синтетические методы

2,2-Diaryl-1,3,2-dioxaborines based on curcumin: synthesis, photophysical properties and preliminary biological studies

Nazarov Alexey A., Dudarova N., Zhidkova O. et al., Journal of Photochemistry and Photobiology A: Chemistry 2026 Vol. 483 Article 117654

Сyclocondensation of phenyl, ortho-bromophenyl, para-phenylphenyl, para-methoxycarbonylphenyl, para-tolyl and para-methoxyphenyl boronic acid with curcumin in the presence of K3PO4 upon refluxing in 1,4-dioxane for 24 h leads to the formation of curcumin-based 2,2-diaryl-1,3,2-dioxaborines in good yields. The absorption-emission spectra of the synthesized fluorescent conjugates and 1,3,2-dioxaborine with para-biphenyl boronic substituent demonstrated the highest quantum yield. Among the compounds studied, conjugate curcumin with para-methoxycarbonylphenyl boronic substituent ...

Added: September 9, 2026

Degree-based topological co-indices for QSPR modelling of benzenoid hydrocarbons: a comparative computational study

Chemical Papers 2026

Benzenoid hydrocarbons are structurally regular aromatic compounds, which makes them well suited for quantitative structure–property relationship (QSPR) studies. This study presents a QSPR analysis of nineteen benzenoid hydrocarbon species using degree-based topological co-indices. We developed a Python program to compute eleven degree-based topological co-indices from molecular graphs and evaluated their ability to explain variations in ...

Added: September 8, 2026

Bridging experiment and molecular dynamics: Mefenamic acid confinement in nanocrystalline cellulose aerogels under scCO2 conditions

Gurina D., Fashchevsky K. A., Oparin R. D. et al., Surfaces and Interfaces 2026 Vol. 98 Article 110545

In this work, we combine experimental characterization and molecular dynamics (MD) simulations to elucidate the molecular mechanisms governing the impregnation of mefenamic acid (MFA) into nanocrystalline cellulose (NCC) aerogels. NCC aerogels were impregnated with MFA in scCO2, and low-temperature nitrogen adsorption revealed a concentration-dependent decrease in surface area, pore volume, and pore size, with an ...

Added: September 8, 2026

Stress tensor of inhomogeneous flexible polymer chain solutions beyond the ground-state dominance approximation

Budkov Y., Journal of Chemical Physics 2026 Vol. 165 No. 9 Article 094902

We derive the stress tensor of a flexible polymer solution within the Gaussian-chain self-consistent field theory (SCFT) without invoking the ground-state dominance (GSD) approximation. Starting from a covariant formulation of the single-chain partition function in a background metric, we obtain the symmetric stress tensor expressed through the full Edwards propagators. The result contains the local ...

Added: September 2, 2026

“-Ethylene” vs “-ethane”: How minor cation variations drive the self-assembly of structurally different supramolecular diiodine-halometalate hybrid complexes

Novikov A., Polyhedron 2026 Vol. 299 Article 118358

Two new supramolecular halometalate hybrid complexes, (H2bpen){[MCl5](I2)} (M = Sb(III) (1) and Bi(III) (2); bpen – 1,2-Bis(4-pyridyl)ethylene, have been prepared. Despite very close similarity of the nature of cations, they reveal significant structural difference from the (H2bpe){[MCl5](I2)} (bpe – 1,2-bis(4-pyridil)ethane) reported earlier. We discuss these features, along with thermal stability, optical properties as well as Raman spectra ...

Added: September 2, 2026

Monometallic Ln3+ and heterometallic Ln3+–Cd2+ complexes based on pentafluorophenylacetic acid: efficient control of dimension and luminescent properties

Belousov Y., Кискин М. А., Sidoruk A. et al., Australian Journal of Chemistry 2022 Vol. 75 No. 9 P. 572–580

Four new complexes [Ln(pfaa)3(H2O)2]n (Ln = Eu (1), Tb (2)) and [Ln2Cd2(pfaa)10 (phen)2(EtOH)2]·2MeCN (Ln = Eu (3), Tb (4), phen = 1,10-phenanthroline) based on pentaphorphenylacetic acid (Hpfaa) have been prepared and completely investigated. The structures of compounds 1 and 3 were studied by single crystal X-ray diffraction analysis: the isostructural complexes 1 and 2 represent ...

Added: August 26, 2026

Understanding the electric double layer at electrode–electrolyte interfaces, Part III: crystallographic-face dependence of silver capacitance in aqueous NaF solutions

Mazur D., Petr E. Brandyshev, Doronin S. et al., Electrochimica Acta 2026 Vol. 577 Article 149729

The electric double layer (EDL) at a single-crystal metal surface is controlled not only by the electrolyte composition and the electrode potential, but also by the atomic structure of the surface itself. This makes the Ag(hkl)/NaF interface a stringent test for continuum theories of the EDL. In the third part of our series, we examine ...

Added: August 20, 2026

Hall effect in electrolyte solutions: Self-consistent Debye–Hückel–Onsager theory

Budkov Y., Kalikin N., Journal of Chemical Physics 2026 Vol. 165 Article 064506

A self-consistent statistical-mechanical theory of the Hall effect in electrolyte solutions is developed by extending the self-consistent Debye–Hückel–Onsager (SCDHO) framework to crossed electric and magnetic fields. The theory incorporates non-local ionic charge distributions via Slater-type form factors, regularizing the Coulomb interaction at short range, and accounts for dielectric friction through ion-specific coefficients, employing experimental values ...

Added: August 12, 2026

Charge-controlled binding, alloy synergy, and the copper anomaly in Au–Ag–Cu dimers to clusters: DFT-derived design rules for targeted drug delivery

Obijiofor O., Alexander S. Novikov, New Journal of Chemistry 2026 Vol. 50 No. 33 P. 13931–13957

The rational design of coinage metal nanocarriers requires a mechanistic understanding of metal-drug binding and predictive descriptors that translate molecular interactions into design rules. Using DFT (B3LYP-D3BJ/def2-TZVP, SMD water), we systematically investigated the binding of 5-fluorouracil (5-FU) and levodopa (l-DOPA) to neutral and cationic homo- and heteronuclear dimers of Au, Ag, and Cu (Au2, Ag2, ...

Added: August 12, 2026

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

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

Recent advances in the synthesis of pharmacologically active 1,2,3-, 1,2,4-, and 1,2,5-oxadiazole-based lead compounds

Стеблецова И. А., Larin A. A., Fershtat L., Russian Chemical Reviews 2025 Vol. 24 No. 10 Article RCR5185

Nitrogen heterocycles hold leading positions in the field of medicinal chemistry and targeted search for next-generation pharmaceuticals. Among the enormous set of available heterocyclic structures, oxadiazole derivatives attract attention of scientists due to a wide range of pharmacological activity, including antimicrobial, antiinflammatory, antiproliferative, and other types of activity. This review summarizes the achievements in the ...

Added: December 1, 2025

Synthesis of 2-aminothiazoles containing 3-hydroxypyran-4-one fragment based on condensation of substituted α-arylaminoketones with thiourea

Komogortsev A. N., Melekhina V. G., Milyutin C. V. et al., Journal of Heterocyclic Chemistry 2024 Vol. 61 No. 10 P. 1531–1541

Condensation of α-arylaminoketones bearing 3-hydroxypyran-4-one fragment with thiourea was studied. Based on considered investigation, the method for the synthesis of terarylenes with 2-aminothiazole bridge was elaborated. The presented process is the first example of construction of thiazole core starting from α-aminoketone precursor. The advantages of developed approach are easily available starting materials and convenient isolation ...

Added: September 14, 2025

3-(3-Azabicyclo[2, 2, 1]heptan-2-yl)-1,2,4-oxadiazoles as Novel Potent DPP-4 Inhibitors to Treat T2DM

Zinevich T., Maslov I., Kirichenko O. et al., Pharmaceuticals 2025 Vol. 18 No. 5 Article 642

Background: Type 2 diabetes mellitus (T2DM) is a prevalent metabolic disease with global implications, necessitating effective management strategies. Dipeptidyl peptidase IV (DPP-4) inhibitors have shown promise as potent agents for T2DM treatment. Methods: This study combines chemical synthesis, molecular modelling, and inhibitory activity assays to characterise the structure–activity relationship of novel isomeric 1,2,4-oxadiazole-substituted derivatives of ...

Added: July 17, 2025

Tandem, Catalyst-Free C−C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite

Korochantsev V., Artemy Fatkulin, Podyacheva E. et al., European Journal of Organic Chemistry 2024 Vol. 28 No. 4 Article e202401108

Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C-C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to ...

Added: January 23, 2025

A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C-Nucleophiles

Fedorenko A., Ivanova V., Minyaev M. E. et al., ChemistrySelect 2023 Vol. 8 No. 43 Article e202303122

General method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3-b]pyridines and benzo[c]thiadiazoles were synthesized. The most π-deficient [1,2,5]thiadiazolo[4,3-b]pyridines readily react with neutral carbon nucleophiles such as CH-acids, indoles, pyrrole and phloroglucinol to give 1,4-adducts. ...

Added: February 14, 2024

Regioselective Synthesis of NO-Donor (4-Nitro-1, 2, 3-triazolyl) furoxans via Eliminative Azide–Olefin Cycloaddition

Stebletsova I., Alexander A. Larin, Ivan V. Ananyev et al., Molecules 2023 Vol. 28 No. 19 Article 6969

A facile and efficient method for the regioselective [3 + 2] cycloaddition of 4-azidofuroxans to 1-dimethylamino-2-nitroethylene under p-TSA catalysis affording (4-nitro-1,2,3-triazolyl)furoxans was developed. This transformation is believed to proceed via eliminative azide–olefin cycloaddition resulting in its complete regioselectivity. The developed protocol has a broad substrate scope and enables a straightforward assembly of the 4-nitro-1,2,3-triazole motif. Moreover, ...

Added: October 12, 2023

Renaissance of dinitroazetidine: novel hybrid energetic boosters and oxidizers

Zhilin E., Ivan V. Ananyev, Pivkina A. et al., Dalton Transactions 2022 Vol. 51 No. 37 P. 14088–14096

Nitrogen-oxygen organic materials constitute an important family of multipurpose high-energy materials. However, the preparation of energetic boosters and oxidizers for various civil and space technologies remains a challenging task and such materials usually require special precautions and fine tunability of their functional properties. To find a balance between energy and safety while retaining the oxidizing ...

Added: October 24, 2022

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

Fershtat, Leonid L., Teslenko F., Synthesis 2021 Vol. 53 No. 20 P. 3673–3682

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 ...

Added: September 12, 2022

Ring Distortion Diversity-Oriented Approach to Fully Substituted Furoxans and Isoxazoles

Чаплыгин D., Gorbunov Y., Leonid L. Fershtat, Asian Journal of Organic Chemistry 2021 Vol. 10 No. 10 P. 2644–2653

A regioselective method for an assembly of pharmacologically relevant fully substituted furoxans and isoxazoles using the ring distortion diversity-oriented approach through the one-pot ring cleavage/nucleophilic addition/oxidation cascade of monosubstituted furoxans was developed. The described synthetic strategy is highly regioselective and provides single furoxan regioisomers upon utilization of N- or S-nucleophiles. Utilization of the cyanide-anion as ...

Added: September 12, 2022