2-Hydroxy-5-sulfobenzoic acid: an efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones

Kiyani, Hamzeh; Darbandi, Hassan; Mosallanezhad, Asiyeh; Ghorbani, Fatemeh

doi:10.1007/s11164-014-1844-x

Cited by 64 publications

(24 citation statements)

References 88 publications

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“…To our knowledge, no other method has been able to generate this type of yield in the case of EWGs under simple and inexpensive conditions. Some authors have in fact described the use of EWGs but could obtain only traces of the desired compounds …”

Section: Resultsmentioning

confidence: 99%

“…They act as inhibitors of the tumor necrosis factor‐alpha . It has been reported that 3,4‐disubstituted isoxazol‐5(4 H )‐one derivatives can be prepared using sodium sulfide in ethanol at room temperature sodium acetate by visible light in aqueous ethanol pyridine in H 2 O under ultrasonic irradiation and also KHP in H 2 O at 50 °C …”

Section: Introductionmentioning

confidence: 99%

“…This catalyst leads to efficient yields (70–98%) using different aromatic aldehydes. Compared to previously published work, this protocol has promising characteristics for the response of the reaction, such as a shorter reaction time, easy treatment, ease of separation of the pure product via simple filtration with high yields, and simplicity of the experimental procedure. This method is operationally simple and eco‐friendly.…”

Section: Introductionmentioning

confidence: 99%

“…15,16 They act as inhibitors of the tumor necrosis factor-alpha. 17,18 It has been reported that 3,4disubstituted isoxazol-5(4H)-one derivatives can be prepared using sodium sulfide in ethanol at room temperature 19 sodium acetate by visible light in aqueous ethanol 20 pyridine in H 2 O under ultrasonic irradiation 21 and also KHP in H 2 O at 50 C. 22 Carbon-carbon and carbon-heteroatom bondforming reactions are the most important reactions in organic synthesis; these reactions are simple, fast, and efficient for chemical synthesis. They have considerable economic and ecological benefits.…”

Section: Introductionmentioning

confidence: 99%

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Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol‐5(4H)‐ones

Ferouani

Nacer

Ameur

et al. 2017

J Chinese Chemical Soc

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An efficient, simple, and green procedure for the synthesis of isoxazol‐5(4H)‐one derivatives are described here through a convenient one‐pot, three‐component reaction at room temperature. The title compounds are isolated in high to excellent yields and after short reaction times, and are characterized by various spectroscopic methods such as IR, 1H NMR, and 13C NMR. The synthesized compounds 4a–c and 4e–i were tested for their in vitro activity against a panel of Gram‐positive and Gram‐negative bacteria, demonstrating their ability to inhibit microorganisms with a zone of inhibition ranging from 15 to 30 mm, minimum inhibitory concentration between 250 and 900 μg/mL, and minimum bacterial concentration between 700 and 1000 μg/mL.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol‐5(4H)‐ones

Ferouani

Nacer

Ameur

et al. 2017

J Chinese Chemical Soc

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“…In addition, the best conversion into the products within short reaction time were achieved by TBAP as compared to glycine and sodium oxalate. [38] . A wide range of solvents like DMSO, ethanol, 1,4-dioxane, dichloromethane, hexane and acetone were also demostrated in this reaction by the authors, although best results were obtained in water in terms of product yield and reaction time.…”

Section: (4h)-onesmentioning

confidence: 99%

Recent Advance in Development of 3-Methyl-4-Arylmethylene Isoxazole-5(4h)-Ones and 6-Amino-1,4-Dihydropyrano[2,3-C]-Pyrazole-5-Carbonitriles: Synthetic Applications and Pathways

Patel¹

2017

WJPPS

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Synthesis and characterization of nanocrystalline hydroxyapatite and its catalytic behavior towards synthesis of 3,4‐disubstituted isoxazole‐5(4H)‐ones in water

Maleki

Chahkandi

Tayebee

et al. 2019

Applied Organom Chemis

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In the present work, the nanocrystalline particles of hydroxyapatite (HAp) using an easy alkoxide‐based sol–gel technique including triethyl phosphate [PO (OC2H5)3] and Ca (NO3)2·4H2O as P and Ca precursors have been synthesized. The sample characterization was performed by X‐ray diffraction, Fourier transform‐infrared analysis, scanning electron microscopy, thermal analysis (thermogravimetric analysis/differential thermal analysis), and elemental analysis of energy‐dispersive X‐ray analysis. It is interesting that single phase of HAp was obtained at a low firing temperature of 500°C. Modified Scherrer equation as the Williamson−Hall method was applied for the measurement of crystallite size distributions and micro‐strain of the sample. The determined crystallite size by complementary technique of transmission electron microscopy has good consistency with those obtained from the Scherrer formula. Moreover, we reported the one‐pot synthesis of 3,4‐disubstituted isoxazole‐5(4H)‐ones through the aqueous solution reaction of three components of ethyl acetoacetate, hydroxylamine hydrochloride and various aromatic aldehydes at room temperature. This protocol offers several advantages, including a simple work‐up procedure, very short reaction times (under 25 min), in accordance with the principles of green chemistry, recyclability, excellent yields (87–98%) and environmentally friendly.

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2-Hydroxy-5-sulfobenzoic acid: an efficient organocatalyst for the three-component synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones

Cited by 64 publications

References 88 publications

Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol‐5(4H)‐ones

Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol‐5(4H)‐ones

Recent Advance in Development of 3-Methyl-4-Arylmethylene Isoxazole-5(4h)-Ones and 6-Amino-1,4-Dihydropyrano[2,3-C]-Pyrazole-5-Carbonitriles: Synthetic Applications and Pathways

Synthesis and characterization of nanocrystalline hydroxyapatite and its catalytic behavior towards synthesis of 3,4‐disubstituted isoxazole‐5(4H)‐ones in water

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