Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-ones in a Deep Eutectic Solvent

Atharifar, Hengameh; Keivanloo, Ali; Maleki, Behrooz

doi:10.1080/00304948.2020.1799672

Cited by 35 publications

(1 citation statement)

References 56 publications

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“…Notably, 4-arylmethylneisoxazol-5(4H)-ones are very useful synthetic intermediates of various applied heterocycles such as pyridopyrimidines 8 , 4-arylpyrrolidones, 1,3-oxazine-6-ones 9 , nicotinates 10 , β-alkylated γ-functionalized ketones 11 and, α-aminopyrrole derivatives 12 . Therefore, these structures have interested organic chemists, and a review of the literature shows a wide variety of homogenous and heterogeneous catalysts and techniques such as sodium acetate 13 , DABCO 14 , modified-MMT 15 , Cu/TCH-pr@SBA-15 16 , L-valine 17 , ZSM-5 18 , DES (ChCl/Gly) 19 , ultrasonic irradiation 20 , Sn(II)-MMT 21 , and ionic liquids 22 . These include the cyclization of O-propioloyl oxime via intermolecular arylidene group transfer 23 , the condensation of 3-phenylisoxazol-5-one within aryl halide, the reaction of 1,3-dicarbonyl compounds with benzaldoximes, and condensation of hydroxylamine with β-keto esters.…”

Section: Introductionmentioning

confidence: 99%

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

Tajbakhsh

Naimi‐Jamal

Saeed

et al. 2022

Sci Rep

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This manuscript reports an impressive and facile strategy for synthesizing isoxazole derivatives using immobilized Cu (I) in metformin-functionalized β-cyclodextrin as a catalyst. The architecture of this catalyst was characterized by different analytical techniques such as Fourier transform infrared spectroscopy, Thermogravimetric analysis, X-ray diffraction, Field emission scanning electron microscopy, and Energy-dispersive X-ray spectroscopy. The catalyst showed remarkable reusability even after 7 consecutive runs.

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Section: Introductionmentioning

confidence: 99%

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

Tajbakhsh

Naimi‐Jamal

Saeed

et al. 2022

Sci Rep

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One‐Step Synthesis of Novel Erlotinib Analogs Catalyzed by Nano‐CuO as Potent Anticancer Agent

Moghadam,

Mokhtary,

Evazalipour

2024

Applied Organom Chemis

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Twenty new substituted erlotinib analogs with anticancer activity were produced with good to excellent yields through the one‐step reaction of erlotinib, aromatic aldehydes, and cyclic secondary amines such as piperidine, morpholine, pyrrolidine, N‐methylpiperazine, or imidazole using nano‐CuO in choline chloride: urea (ChCl:urea) solvent under ultrasound irradiation at 80°C. MTT protocol was applied to investigate the cytotoxicity of all produced substituted erlotinib analogs in A431 (human epidermoid carcinoma cell) and HU02 (foreskin fibroblast) cell lines. The results illustrated that at a concentration of less than 10 μM, the growth of A431 cells could be inhibited by the produced compounds. Compared to erlotinib as positive control, the highest cytotoxic activity with IC50 equal to 2.58 ± 0.57 μM belonged to compound 4c carrying 4‐fluorobenzene with piperidine substitution. All of the synthesized compounds showed significant cytotoxic activity on A431, while showing no apparent cytotoxicity to HU02. The reasons for the stronger cytotoxic activity 4c can be most probably attributed to the two phenomena of greater solubility of the fluoro derivative and the flexibility of piperidine. Based on this study, compound 4c is the most promising compound with anticancer properties.

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Environmentally Benign and Expeditious Access to 4‐Aryl Methylene‐isoxazole‐5(4H)‐Ones Using Magnetically Separable Nanoparticles

Dhirbassi,

Tangade,

Kauthale

et al. 2024

ChemistrySelect

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An environmentally benign and expeditious protocol was developed for the one‐pot multicomponent synthesis of 4‐aryl‐3‐methylisoxazol‐5(4H)‐ones by the condensation of aldehyde, hydroxyl amine hydrochloride, and ethyl acetoacetate in 50% aq. ethanol at 50 °C. The reaction was catalyzed by magnetically separable carbon microspheres co‐decorated with nanosized iron sulfide and magnetite nanoparticles in 10 wt% amount. The FeS1‐x‐Fe3O4/C nanocatalyst was prepared from iron(III) sulfate loaded iminodiacetate group functionalized styrene‐divinylbenzene based ion exchanger by pyrolysis reaction performed at 600 °C for 4 h. The use of magnetically separable heterogeneous catalyst, aqueous ethanol, short reaction time (30 min), and nonchromatographic purification methods are the striking features of the developed protocol. The isolated yield of the condensation products varied between 81% and 96%. Furthermore, the protocol exhibits high functional group tolerance and includes the use of noncorrosive, nonhazardous reaction conditions affording the product in excellent yields and short reaction time.

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Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-ones in a Deep Eutectic Solvent

Cited by 35 publications

References 56 publications

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

One‐Step Synthesis of Novel Erlotinib Analogs Catalyzed by Nano‐CuO as Potent Anticancer Agent

Environmentally Benign and Expeditious Access to 4‐Aryl Methylene‐isoxazole‐5(4H)‐Ones Using Magnetically Separable Nanoparticles

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