Empowering strategies of electrochemical N–N bond forming reactions: direct access to previously neglected 1,2,3-triazole 1-oxides

Titenkova, Kseniia Yu; Shuvaev, Alexander D.; Teslenko, Fedor E.; Zhilin, Egor S.; Ферштат, Леонид Л.

doi:10.1039/d3gc01601c

Cited by 11 publications

(1 citation statement)

References 54 publications

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“…Moreover, biomedical applications of simple heterocyclic NO donors along with their hybridization with other pharmacophoric scaffolds were found to be promising for the creation of new medications to overcome the issue of multidrug resistance [15][16][17]. A variety of heterocyclic NO donors (furoxans [18][19][20][21][22], azasydnones [23,24], sydnone imines [25], triazole oxides [26] and pyridazine dioxides [27]) were synthesized and evaluated for their pharmacological potency so far (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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

Stebletsova,

Larin,

Ananyev

et al. 2023

Molecules

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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, synthesized (4-nitro-1,2,3-triazolyl)furoxans were found to be capable of NO release in a broad range of concentrations, thus providing a novel platform for future drug design and related biomedical applications of heterocyclic NO donors.

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Section: Introductionmentioning

confidence: 99%

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

Stebletsova,

Larin,

Ananyev

et al. 2023

Molecules

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Electrochemical Approach Toward Mesoionic 1,2,3‐Triazole 1‐Imines

Shuvaev,

Feoktistov,

Teslenko

et al. 2024

Adv Synth Catal

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Synthetic electrochemistry may establish direct routes to a preparation of a plethora of organic substances, which are hardly accessible by conventional experimental techniques. Herein, we present an electrochemically‐driven method for an assembly of a broad range of rare heterocyclic mesoionic entities – 1,2,3‐triazole 1‐imines. These nitrogen heterocycles were prepared through a transition‐metal‐ and exogenous oxidant‐free strategy using a C/Ni electrode pair. Over 30 examples of thus synthesized 1,2,3‐triazole 1‐imines illustrate selectivity and practical utility of this approach. Key solvent‐controlled reactivity patterns for the formation of the triazole imine scaffold were revealed indicating a modulation ability of the developed approach. These experimental findings were additionally justified based on cyclic voltammetry (CV) data and density functional theory (DFT) calculations. Moreover, according to differential scanning calorimetry (DSC) data, some of the prepared 1,2,3‐triazole 1‐imines correspond to the thermally stable species with an onset decomposition temperature up to 190 oC.

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Novel Eco‐Friendly Electrode: Copper Nanoparticle‐Doped MWCNTs for Green Electro‐Organic Synthesis of 1,2,3‐Triazoles With ChCl/Urea as a Solvent and Cocatalyst

Basem,

Sagdullaev,

Alaridhee

et al. 2024

Applied Organom Chemis

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Meticulous electrode design is pivotal in advancing greener and more sustainable electro‐organic synthesis practices. In this research, our team designed and synthesized a copper‐doped electrode on multiwalled carbon nanotubes (MWCNTs) and characterized it using Fourier transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDS), thermogravimetric analysis (TGA), Brunauer–Emmett–Teller (BET) analysis, X‐ray diffraction (XRD) analysis, X‐ray photoelectron spectroscopy (XPS), and cyclic voltammetry (CV) analysis. Subsequently, this electrode was utilized as a catalyst at the electrode surface, serving as a cathode in electro‐oxidation reactions in the presence of phenylacetylene, sodium azide (NaN3), and benzyl halide for the production of 1,2,3‐triazole derivatives under ambient temperature, within a 30‐min reaction time, and at atmospheric pressure, achieving an efficiency level ranging from good to excellent, specifically between 88% and 96%. The synthesized 1,2,3‐triazole derivatives were identified using proton nuclear magnetic resonance (1H NMR) spectroscopy, CHN elemental analysis, and melting point. In this paper, choline chloride/urea deep eutectic solvents (DES) serve multiple roles in the reaction mechanism. They function as solvents and co‐catalysts, generate weak bases, and provide numerous advantages in green chemistry. These advantages include low toxicity, reduced environmental risks, improved atom economy, and non‐volatility, making them safer alternatives to traditional organic solvents.

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Empowering strategies of electrochemical N–N bond forming reactions: direct access to previously neglected 1,2,3-triazole 1-oxides

Abstract: Electrochemical synthesis became one of the emerging and powerful tools to create novel state-of-the-art strategies for an assembly of complex organic molecules. However, electrochemically-induced N-N bond forming reactions still remain...

Cited by 11 publications

References 54 publications

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

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

Electrochemical Approach Toward Mesoionic 1,2,3‐Triazole 1‐Imines

Novel Eco‐Friendly Electrode: Copper Nanoparticle‐Doped MWCNTs for Green Electro‐Organic Synthesis of 1,2,3‐Triazoles With ChCl/Urea as a Solvent and Cocatalyst

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