Ultrasound accelerated solvent-free condensation reaction of rhodanines and carbonyls using Amberlyst 26 as a green and efficient base catalyst

Nguyen, Duc-Thuan; Pham, Ngoc-Khoi; Nguyen, Xuan-Triet; Luu, Thi Xuan Thi; Luong, Quynh-Nhi Nguyen

doi:10.1080/17415993.2023.2173008

Cited by 4 publications

(4 citation statements)

References 34 publications

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“…3i 72% Amberlyst 26, ultrasound irradiation, 60 °C, 6 h 75% [42] compounds for their antioxidant activity expressed as percentage of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity. DPPH free radicals give a purple solution and present a strong absorption maximum at 517 nm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

Hesse

2023

Beilstein J. Org. Chem.

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Rhodanines and their derivatives are known to have many pharmacological activities that can be modulated through different functionalization sites. One of the most studied modification in those scaffolds is the introduction of a benzylidene moiety on C5 via a Knoevenagel reaction. Here, a facile synthesis of 5-arylidenerhodanines via a Knoevenagel reaction in an ʟ-proline-based deep eutectic solvent (DES) is reported. This method is fast (1 h at 60 °C), easy, catalyst-free and sustainable as no classical organic solvents were used. The expected compounds are recovered by a simple filtration after hydrolysis and no purification is required. Those derivatives were studied for their antioxidant activities and the results are consistent with those reported in the literature indicating that phenolic compounds are the more active ones.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

Hesse

2023

Beilstein J. Org. Chem.

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“…The methylene group in rhodanine derivatives 10 is highly active and, upon interaction with furfural and its substituted derivatives 11 in the presence of basic catalysis, easily forms the target (5E)-3-R 1 -5-[(5-R-furan-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-ones 12 (Scheme 3). [1][2][3][23][24][25][26] The geometric placement of substituents at the 5-th position of the rhodanine ring of the above compounds has not been studied separately. However, by analogy with other 5-arylidenerhodanines, it can be argued that this is the Z-configuration 1-3 .…”

Section: Methods Of Construction Of the Rhodanine (2-thioxothiazolidi...mentioning

confidence: 99%

Synthesis and biological activity of rhodanine-furan conjugates: A review

Matiichuk,

Drapak,

Darmograi

et al. 2024

10.5267/j.ccl

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Rhodanines are recognized as privileged heterocycles in medicinal chemistry. The main achievements include the development of drug-like molecules with numerous biological activities as well as approved drugs. The Furan nucleus is considered one of the promising heterocyclic cores in medicinal chemistry that showed numerous ranges of activity. The combination of several heterocycles in a one molecule commonly provides much more interest in the enhanced activity profile of its analogs than their parent separate constituents. Such conjugates are promising objects for modern medicinal chemistry. In this review paper recent advances in the synthesis and biological activities rhodanine-furan conjugates which its application in the different field of drug discovery.

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“…Compounds 1a-7a are described in Reference [20]. [33,36] Yellow solid obtained after 1 h at 60 C in 72% yield (117 mg). Mp = 250 C. Orange-brown solid obtained after 3 h at 60 C in 85% yield (132 mg).…”

Section: General Procedures For the Knoevenagel Condensationmentioning

confidence: 99%

L‐proline‐based DES in Knoevenagel synthesis of arylidene rhodanines, thiazolidine‐2,4‐diones, and barbituric derivatives

Hesse,

Hertzog,

Rup‐Jacques

2024

Journal of Heterocyclic Chem

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Deep eutectic solvents (DES) are environmentally friendly solvents that prevent the use of toxic organic solvents and have been extensively studied in recent years. However, volatile organic compounds (VOC) are often still used during workup and isolation of products. Here, a zero‐VOC strategy for Knoevenagel reaction is reported. (Hetero)aromatic aldehydes are successfully condensed with rhodanine, thiazolidine‐2,4‐dione TZD, or barbituric acid under mild conditions in an L‐proline‐based DES and pure compounds are obtained after hydrolysis without any purification. For the less reactive TZD, activation by microwave allows diminution of reaction time from 24 h to just 1 h.

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Ultrasound accelerated solvent-free condensation reaction of rhodanines and carbonyls using Amberlyst 26 as a green and efficient base catalyst

Cited by 4 publications

References 34 publications

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

Synthesis and biological activity of rhodanine-furan conjugates: A review

L‐proline‐based DES in Knoevenagel synthesis of arylidene rhodanines, thiazolidine‐2,4‐diones, and barbituric derivatives

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