Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition

Jadhav, Santosh; Sarkate, Aniket P.; Farooqui, Mazahar; Shinde, Devanand B.

doi:10.1080/00397911.2017.1340649

Cited by 7 publications

(5 citation statements)

References 25 publications

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“…The white formed precipitate was collected by filtration and washed out with water (negative reaction for chloride). The spectral data was in agreement with literature data [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ].…”

Section: Methodssupporting

confidence: 90%

“…Also, the configuration of the ring opened products is the same as that of the parent oxazolone [ 32 ]. Compounds 2a , 2c , 2d , 2e , 2f , 3a , 6c have been synthesized previously under different experimental conditions [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ]. The structures of the new compounds were confirmed by IR, 1 H-NMR, MS (ΕSI) and elemental analysis and they were found to be consistent with the proposed structures.…”

Section: Resultsmentioning

confidence: 99%

“…(Z)-4-Benzylidene-2-phenyloxazol-5(4H)-one ( 2a ) [ 35 , 36 , 37 , 38 , 41 ]. Yield: 67%; R f = 0.8 (CH 3 COOC 2 H 5– petroleum ether, 6:1); m.p.…”

Section: Methodsmentioning

confidence: 99%

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5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

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The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer–Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94% and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5%. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a–4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.

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Section: Methodssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

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5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

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“…They serve as intermediates and suitable building blocks for the production of a variety of physiologic active compounds like amino acids and heterocyclic compounds [4][5][6]. In addition, these compounds are particularly effective as antioxidants [7], antitumors [8], antimicrobials [9], and antihypertensives [10] agents. The Erlenmeyer method is the most used method for creating oxazolones [11], which includes a condensation reaction of hippuric acid or its derivatives with aryl aldehydes in dehydrating agent as acetic anhydride and basic catalyst as anhydrous sodium acetate [12].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4H)-oxazolone Derivatives

Saadi,

Adnan

2023

Indones. J. Chem.

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In this research, the synthesis of new substituted oxazolone derivatives is described via Erlenmeyer synthesis of N-acyl amino acid. Firstly, the azo derivative 1 was prepared by coupling the diazonium salt of 3-amino-4-methoxybenzoic acid with 4,5-dichloroimidazole in sodium hydroxide solution. Benzoyl chloride derivative 2, the key intermediate of the synthesis, was synthesized by the acylation of azo-carboxylic acid derivative 1 with thionyl chloride. The resulting acyl chloride derivative reacted with glycine in a basic catalyst to form a hippuric acid derivative 3. After that, oxazolone derivatives 4a–4f were prepared via the reaction of the hippuric acid derivative with various aromatic aldehydes. All new compound structures were confirmed by spectral techniques, i.e., FTIR, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. The antimicrobial activity (Staphylococcus aureus and Escherichia coli) of all new compounds was screened in vitro. The results against S. aureus and E. coli showed that most of the tested compounds have an activity ranging from moderate to low. The antioxidant activity of derivative 4a was also evaluated and showed good antioxidant activity.

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“…As a part of our ongoing program in the development of environmentally benign and sustainable process , herein, we wish to report a straightforward one‐pot three‐component reaction of substituted isatin, active methylene group, and 4‐hydroxycoumarin in γ‐valerolactone for the synthesis of spirooxindoles with fused pyrano[3,2‐ c ]chromene derivatives. To the best of our knowledge, there is no report available in the literature for the synthesis of spirooxindoles with fused pyrano[3,2‐ c ]chromene derivatives using γ‐valerolactone as green and reusable bio‐based solvent (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

γ‐Valerolactone as a Promising Bio‐Compatible Media for One‐Pot Synthesis of Spiro[indoline‐3,4'‐pyrano[3,2‐c]chromene Derivatives

Diwan¹,

Farooqui²

2018

Journal of Heterocyclic Chem

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A general, highly efficient, and green protocol for the synthesis of biologically important spiro[indoline-3,4 0 -pyrano[3,2-c]chromene derivatives is developed by one-pot, three-component approach involving substituted isatin, active methylene group, and 4-hydroxy coumarin. This report describes the use of γvalerolactone as a green reaction media for a variety of substrates. The advantageous features of this methodology are the environmentally benign character, operational simplicity, high yield processing (91-96%), easy handling, and the reaction medium can be recycled and reused several times without significant loss of its efficiency. White solid;Scheme 3. Plausible mechanism of spiro[indoline-3,4 0 -pyrano[3,2-c]chromene derivatives 4a-q. [Color figure can be viewed at wileyonlinelibrary.com] 2820 F. Diwan and M. Farooqui

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Greener approach: Ionic liquid [Et₃NH][HSO₄]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition

Cited by 7 publications

References 25 publications

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives

γ‐Valerolactone as a Promising Bio‐Compatible Media for One‐Pot Synthesis of Spiro[indoline‐3,4'‐pyrano[3,2‐c]chromene Derivatives

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