An Expedient Four Component Synthesis of Substituted Pyrido-Pyrimidine Heterocycles in Glycerol:Proline Based Low Transition Temperature Mixture and Their Antioxidant Activity with Molecular Docking Studies

Mohire, Priyanka P.; Chandam, Dattatray; Patravale, Ajinkya A.; Choudhari, Prafulla; Karande, Vishram; Ghosh, Jai S.; Deshmukh, M. B.

doi:10.1080/10406638.2020.1720749

Cited by 15 publications

(6 citation statements)

References 56 publications

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“…In fact, the exact role of DES in this reaction is still not clear as ʟ-proline may act as a catalyst via an iminium pathway as previously described [ 21 – 22 ]. On the other hand, Pro/Gly DES may also activate carbonyl groups as suggested by Mohire et al [ 23 ] and Theresa et al . [ 24 ].…”

Section: Resultsmentioning

confidence: 91%

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: 91%

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

Hesse

2023

Beilstein J. Org. Chem.

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“…It has been shown that glycerol can form a strong hydrogen bonding network in a DES, being here an H‐bond donor and L‐proline being an H bond acceptor [32, 33]. A plausible mechanism often proposed by the authors [25, 27–31] involves the activation of carbonyl group by the DES (Scheme 1). Another point to be considered is the fact that it is well established that L‐proline forms iminium ion with aldehyde to catalyze Knoevenagel condensation [34, 35] (Scheme 2).…”

Section: Resultsmentioning

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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“…Pyridopyrimidines and relevant fused heterocycles are of importance as potential bioactive molecules. They have been extensively applied in medicinal, 1,2 and biological chemistry [3][4][5] due to the range of their available products that includes vast chemical variety and their ve feasible substitution localities. 6 Hollow nanostructures are a group of specic nanomaterials identied based on their morphologies.…”

Section: Introductionmentioning

confidence: 99%