Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton

iScience, Journal Year: 2025, Volume and Issue: 28(3), P. 111976 - 111976

Published: Feb. 10, 2025

1,n-Dual Π systems including 1,4-diene derivatives have been widely used as the elegant radical receptors to promote cascade additions give highly functionalized polycyclic scaffolds. However, tedious and complicated preparation of former deters broad utilization compromises practical value. Herein, a straightforward was developed from easily accessible alkynes γ,δ-unsaturated carboxylic acids via electrochemical oxidation cyclization Hofmann elimination. This transformation features with good excellent yields, functional group compatibility, selectivity without any Zaitsev elimination product detected.

Language: Английский

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Electrooxidative synthesis of 1,2,3-triazolone 1-amines

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel sustainable electrochemical approach for the selective intramolecular formation of N–N bonds via oxidation readily available α-aminocarbonyl hydrazones was realized.

Language: Английский

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Synthesis of Rare 1,2,3-Triazolium-5-olates by Electrooxidative Cyclization of α-Aminocarbonyl Hydrazones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

A new method for the synthesis of rare mesoionic heterocycles, namely, 1,2,3-triazolium-5-olates, via electrochemically induced intramolecular N-N bond formation was realized. The process involves electrooxidative cyclization readily available α-aminocarbonyl hydrazones, occurs under mild conditions, and enables preparation a diverse series target mesoionics. Additionally, 1,2,3-triazolium-5-olates demonstrated high thermal stability (up to 275 °C) feature prominent Stokes shifts (7600-8050 cm-1), which their application potential analytical systems materials science.

Language: Английский

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

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 22, 2024

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

Language: Английский

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Photo- and Electro-chemical Strategies for Indazole Synthesis

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: unknown, P. 100116 - 100116

Published: Dec. 1, 2024

The indazole core is prevalently found in the structures of bioactive molecules, demonstrating promising potential medicinal chemistry and drug discovery, which therefore has attracted sustained attention from synthetic community. Over recent decades, significant progress been achieved both organic photocatalysis electrosynthesis, offering novel approaches for efficient sustainable synthesis various functionalized indazoles. This mini-review highlights emerging methodological advancements photo-/electro-chemical two common forms indazole, namely 1H- 2H-indazoles, are classified by specific intramolecular bond formation patterns: (1) C-C formation, (2) C-N (3) N-N formation. reaction conditions, representative scopes, mechanistic understandings these protocols emphasized, to elucidate advantages limitations current strategies, with an aim inspire future innovations that may address challenges modern synthesis.Graphical abstractTo create your abstract, type over instructions template box below. Fonts or abstract dimensions should not be changed altered.

Language: Английский

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Ammonium Dinitramide as a Prospective N–NO2 Synthon: Electrochemical Synthesis of Nitro-NNO-Azoxy Compounds from Nitrosoarenes

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5563 - 5563

Published: Nov. 25, 2024

In this study, the electrochemical coupling of nitrosoarenes with ammonium dinitramide is discovered, leading to facile construction nitro-

Language: Английский

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