Solvent-Regulated Cyclization of Arylidene Isoxazolones with Amidines for Regiodivergent Synthesis of 4- and 5-Acylimidazoles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 27, 2025

N-Iodosuccinimide-promoted cascade reactions of arylidene isoxazolones with amidines in p-xylene were accomplished, affording 5-acylimidazoles good to excellent yields. Interestingly, when the performed by employing acetonitrile as solvent, 4-acylimidazoles efficiently obtained. Mechanistic studies indicate that formation imidazolyl and acyl moieties may undergo a spiroannulation-ring opening aromatization-hydrolysis reaction sequence. Based on this solvent-regulated tandem strategy, powerful protocol for switchable regiodivergent synthesis structurally diverse was successfully established.

Language: Английский

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Synthesis of CF₃-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3 + 2] Cyclization Reaction

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15282 - 15287

Published: Oct. 12, 2023

We report herein a general and effective system achieving cyclization of β-trifluoromethyl enones with amidines in the presence 1,3-diiodo-5,5-dimethylhydantoin (DIH), which affords range trifluoromethylated 2-imidazolines synthetically useful yields good diastereoselectivities (up to 95% yield, up 98:2 dr) functional group tolerance. Furthermore, one-pot synthesis imidazoles via sequential oxidation is demonstrated. More significantly, reaction mechanism was verified by ESI-MS studies possible intermediates, reasonable proposed.

Language: Английский

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Magnetically Reusable Fe3O4‐CuO Nanoparticles as Catalysts for the Synthesis of Aryl‐Substituted Fluorescent Pyrazines for Fe Sensing and Ink Applications

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)

Published: June 18, 2024

Abstract The synthesis of substituted pyrazines from readily available methyl aryl/heteroaryl ketones and 1,2‐diamines was achieved using highly stable reusable ferrite‐stabilized copper nanoparticles (Fe 3 O 4 ‐CuO) as a catalyst. reaction proceeds through cascade imine formation–oxidative cyclization method under an oxygen atmosphere. nanocatalysts were recovered reused up to three consecutive cycles without any significant decrease in particle size, catalytic activity yield, evidenced by analytical techniques such transmission electron microscopy (TEM) powder X‐ray diffraction (PXRD). synthesized exhibited photophysical behaviour, displayed large Stokes shifts, explored fluorescent probes for the sensitive well selective “turn‐off” detection iron with limit 0.63 μM. sensing is also useful quantification spiked water samples. Furthermore, application luminescent ink successfully demonstrated.

Language: Английский

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Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3727 - 3727

Published: Jan. 1, 2024

Language: Английский

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