Ruthenium–Hydride Complexes Facilitated Sustainable Synthesis of Isoxazolones via Acceptorless Dehydrogenative Annulation of Alcohols

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

Published: Jan. 1, 2025

A streamlined strategy for the one-pot synthesis of isoxazolone analogues has been developed through an acceptorless dehydrogenative annulation (ADA) pathway by employing new Ru(II) hydride complexes as effective catalysts. New (C1–C3) tailored with N̂O chelating carbazolone benzhydrazone ligands were synthesized and their formation was confirmed using analytical spectral techniques including FT-IR NMR. The structural configuration featuring octahedral geometry around ion precisely determined single-crystal X-ray diffraction analysis. Further, catalytic efficacy titled established facile productive derivatives from a diverse range benzyl alcohols, methyl acetoacetate/ethyl benzoylacetate hydroxylamine hydrochloride, generating excellent yields up to 93% under well-suited mild conditions 1 mol % catalyst loading. sequence time-dependent control experiments unveiled ADA route, indicating initial generation 4-methoxy benzaldehyde intermediate followed 3-phenylisoxazol-5(4H)-one, accompanied release water hydrogen byproducts. Gram-scale compound indicates industrial relevance our synthetic strategy. short medicinally active androgen antagonist illustrates utility present protocol.

Language: Английский

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One-pot three-component synthesis of azaspirononatriene derivatives

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 30, 2025

The present investigation has introduced a new class of isocyanide/acetylene-based multicomponent reactions (IAMCRs). These are robust technique for efficiently synthesizing intricate spiro architectures through zwitterionic adduct. coupling reaction between the "in situ" generated dipoles isocyanide-acetylenic ester adducts and 3-alkyl-4-arylidene-isoxazol-5(4H)-one derivative presents highly effective synthetic pathway obtaining novel 1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene heterocycles. broad range substrates, standard experimental conditions, straightforward procedure, impressive yields make our catalyst-free three-component approach practical green, as it remarkably offers step-, time- cost-effectiveness based on green metrics.

Language: Английский

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Efficient synthesis of isoxazole-5(4H)-ones and polyhydroquinolines using MMWCNTs-PIP and MMWCNTs-MOR

Research on Chemical Intermediates, Journal Year: 2025, Volume and Issue: unknown

Published: March 29, 2025

Language: Английский

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Synthesis of Isoxazol-5-One Derivatives Catalyzed by Amine-Functionalized Cellulose

Published: Aug. 27, 2024

In this contribution, the propylamine-functionalized cellulose (Cell-Pr-NH2) was employed as catalyst in three-component reaction between hydroxylamine hydrochloride, various type of aryl/heteroaryl aldehydes, ethyl acetoacetate/ethyl 4-chloroacetoacetate/ or 3-oxohexanoate. The results these experiments were formation 3,4-disubstituted isoxazol-5(4H)-one heterocycles. desired five-membered heterocyclic compounds obtained good to high yields at room temperature. investigation different solvents led us conclusion that water is best solvent perform current one-pot, reactions. Attempts find optimum loading clearly showed 14 mg Cell-Pr-NH2 seems be sufficient carry out This method has highlighted some principles green chemistry including less waste generation, atom economy, use an environmentally friendly solvent, and energy saving. Purification without chromatographic methods, mild conditions, simple work-up, low-cost medium, saving time, obtainable precursors are other notable features one-pot fashion.

Language: Английский

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Facile synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations, IR and UV–visible spectra analyzes, ADMET and molecular docking studies of arylideneisoxazolone derivatives

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1317, P. 139005 - 139005

Published: June 18, 2024

Language: Английский

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Synthesis of Isoxazol-5-One Derivatives Catalyzed by Amine-Functionalized Cellulose

Organics, Journal Year: 2024, Volume and Issue: 5(4), P. 378 - 394

Published: Oct. 12, 2024

In this contribution, propylamine-functionalized cellulose (Cell-Pr-NH2) was employed as the catalyst in three-component reaction between hydroxylamine hydrochloride and various types of aryl/heteroaryl aldehydes, ethyl acetoacetate/ethyl 4-chloroacetoacetate, or 3-oxohexanoate. The result these experiments formation 3,4-disubstituted isoxazol-5(4H)-one heterocycles. desired five-membered heterocyclic compounds were obtained good to high yields at room temperature. investigation different solvents led us conclusion that water is best solvent perform current one-pot, reactions. Attempts find optimal loading clearly showed 14 mg cell-Pr-NH2 seems be sufficient carry out This method has highlighted some principles green chemistry including less waste generation, atom economy, use an environmentally friendly solvent, energy saving. Purification without chromatographic methods, mild conditions, simple work-up, low-cost medium, saving time, obtainable precursors are other notable features one-pot fashion.

Language: Английский

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Magnetic Mwcnts Immobilized Ionic Liquid Catalyzed Efficient Multi-Component Synthesis of 3-Methyl-4-Arylmethylene Isoxazole-5(4h)-Ones and Polyhydroquinolines

Published: Jan. 1, 2024

Language: Английский

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