An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

Rayar, Anita Maria; Veitía, Maité Sylla-Iyarreta; Ferroud, Clotilde

doi:10.1186/s40064-015-0985-8

Cited by 19 publications

(12 citation statements)

References 25 publications

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“…These microwave-assisted condensation reactions could be "directly scalable". Identical yields were obtained on 50 mg and 500 mg scale [22].…”

Section: Synthesismentioning

confidence: 59%

“…After irradiation, reactions were controlled by GC-MS analysis, and the purity of the desired products was evaluated by NMR spectroscopy. All synthetic details of microwave activation procedure and the extension of these conditions to the synthesis of various benzalacetones have been previously described by our research group [22]. The use of microwave activation resulted in a dramatic decrease of reaction times.…”

Section: Synthesismentioning

confidence: 99%

“…The organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to obtain the corresponding benzalacetone. The purity of the final products was controlled by NMR [22].…”

Section: General Procedures For the Microwaveassisted Synthesesmentioning

confidence: 99%

See 2 more Smart Citations

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

Rayar¹,

Goya-Jorge

Barigye

et al. 2015

Proceedings of MOL2NET, International Conference on Multidisciplinary Sciences

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The α,β-unsaturated ketones known as benzalacetones are an interesting class of compounds frequently used as key intermediates in organic synthesis. Due to their conjugated system, benzalacetone and derivatives have been described as radical scavengers with potential antioxidant properties. We report here a simple and direct method to prepare functionalized α,βunsaturated ketones via a microwaves activated Claisen-Schmidt reaction. The experimental protocol developed selectively produces benzalacetones without self-condensation product in very short reaction times and good yields. Interested in the biological properties of benzalacetones, we also studied the antioxidant potential of these compounds using an in silico study based on the DPPH• radical scavenging ability. The built mathematical model was based on the 0-3D DRAGON molecular descriptors and the artificial neural networks technique showing a correlation coefficient for the training set (2) = 0.71 , an external correlation coefficient (2) = 0.65. Unfortunately, the results obtained in the in-silico study revealed that SciForum Mol2Net, 2015, 1(Section B), pages 1-8, Proceedings 2 http://sciforum.net/conference/mol2net-1 synthesized benzalacetones have no antioxidant activity. The predicted results have been confirmed experimentally by an in vitro assay of DPPH• scavenging capacity.

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“…These microwave-assisted condensation reactions could be "directly scalable". Identical yields were obtained on 50 mg and 500 mg scale [22].…”

Section: Synthesismentioning

confidence: 59%

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

Rayar¹,

Goya-Jorge

Barigye

et al. 2015

Proceedings of MOL2NET, International Conference on Multidisciplinary Sciences

Self Cite

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“…Chemistry: The starting materials (1a-e) and (2) were prepared according to a reported procedure and their structures were confirmed by comparison of its physical and spectral data with the reported ones 19,20 . The synthesis of aryloxyacetic acid derivatives containing 2-chloroquinoline chalcone 3a-e was accomplished using the reported simple and fast method 22 . This method involves a one-pot base catalyzed Claisen-Schmidt condensation of compound 2 with 2-chloroquinoline-3-carbaldehyde derivatives1a-using aqueous NaOH as a base in the presence of ethanol as a solvent Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…The target compounds 4a-e were prepared by treating 3a-e with aqueous acetic acid as a solvent under reflux to afford the desired 2-Oxo-1,2dihydroquinoline derivatives 4a-e Scheme 1. IR, NMR spectroscopy and elemental analyses, confirmed structures of chalcones 4a-e. 22 . Results of the antibacterial activity Table 1 indicated that S. aureus and M.…”

Section: Scheme 1: Synthesis Of Target Compounds 3a-e and 4a-ementioning

confidence: 99%

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2019

IJPSR

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A series of new quinoline/chalcone hybrids 3a-e and 4a-e were designed and synthesized. The structures of all new target molecules 3a-e and 4a-e have been confirmed by various spectral techniques and elemental analyses. The newly synthesized compounds were screened for their antibacterial activity using agar disc diffusion method. Results showed that most of the newly synthesized compounds showed good antibacterial activity comparable with that of the standard drug Gatifloxacin against all tested strains (B. cereus, E. coli, and S. marcescens) except for P. aeroginosa where it does not respond to most of the newly synthesized compounds, and that compounds 3c, 4c, 4d, and 4e showed good antibacterial activity (53-78% that of Gatifloxacin) towards some bacterial strains (Bacillus cereus, Escherichia coli, and Serratia marcescens) when compared to standard drug Gatifloxacin. Amongst all the tested compounds, 4e exhibited excellent activity against S. marcescens (88% that of Gatifloxacin).

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Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

et al. 2018

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A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals.

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An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

Cited by 19 publications

References 25 publications

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

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Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

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