Solvent free synthesis of 1,3-diaryl-2-propenones catalyzed by commercial acid-clays under ultrasound irradiation

Chtourou, Mohamed; Abdelhédi, Rami; Frikha, Mounir; Trabelsi, Mahmoud

doi:10.1016/j.ultsonch.2009.06.008

Cited by 40 publications

(20 citation statements)

References 26 publications

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“…Changes in its structure proved to be very useful for the development of new medicinal agents with improved potency and lower toxicity [4]. As is well known, chalcones (3) are commonly synthesized by Claisen-Schmidt condensation, which involves cross aldol condensation of appropriate aldehydes (1) and ketones (2) by base catalysed or acid catalysed reactions followed by dehydration. Scheme 2.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Syntheses of Chalcones: Experimental Design and Optimization

Cancio¹,

Costantino²,

Silbestri³

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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Chalcones are a group of compounds that belong to the flavonoid family and have a wide variety of uses, including a high therapeutic potential for multiple diseases, such as, anticancer, antifungal or antibacterial agents. As is well known, chalcones are commonly synthesized by Claisen-Schmidt condensation, aldol condensation involving the appropriate aldehydes and ketones, in presence of acid or base as catalyst followed by dehydration reactions. However, under conventional conditions it is carried out with prolonged reaction times and requires expensive catalysts. For this reason, alternative source of energy, microwave or ultrasound, are employed. On the other hand, in all chemical processes a considerable amount of variables (instrumental parameters, reagents, temperatures, times, etc.) take part so a large number of experiments must be carried out in order to define the optimal conditions. In addition, the experimental design technique -important tool-allows the optimization of conditions leading to better yields in shorter times. Here and in line with previous research, we explore the synthesis, assisted by ultrasound, of (E)-1,3diphenyl-2-propen-1-one like a model reaction. Taguchi Design was the mathematical method employed to determine the best working condition. In conclusion, the desired product is obtained quantitatively, without undesired by-products, and in short reaction times. Additionally, the reaction was used, as an alternative method, to monitor the ultrasound equipment using the control chart methodology (Shewhart chart), which allowed us to study how a process changes over time.

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Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Syntheses of Chalcones: Experimental Design and Optimization

Cancio¹,

Costantino²,

Silbestri³

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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“…In recent years, various heterogeneous catalysts have been used for the synthesis of chalcones, such as alkaline‐doped carbons, zeolites, alumina, magnesium oxide, hydrotalcites, natural phosphates modified with sodium nitrate or potassium fluoride, potassium hydroxide impregnated on silica gel, acid montmorillonites, silica–sulphuric acid, zinc chloride and microwave irradiation, commercial acid clays, metal nanoparticles and AlSBA‐15‐SO 3 H . These methods, however, have certain disadvantages like complicated preparation of the catalyst or the use of expensive toxic solvents to facilitate heat and mass transfer in liquid‐phase reaction systems.…”

Section: Introductionmentioning

confidence: 99%

Piperidine‐functionalized silica: an efficient and environmentally benign catalyst for Claisen–Schmidt condensation

Khan

Siddiqui

2014

Applied Organom Chemis

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Piperidine‐functionalized silica as a basic heterogeneous catalyst was synthesized via a simple protocol by condensing silica chloride with piperidine. The catalyst was characterized with various techniques (FT‐IR, solid state NMR, scanning electron microscopy, energy‐dispersive X‐ray, thermogravimetric, elemental, and NH3 and CO2 temperature‐programmed desorption analyses). Surface area was also evaluated through Brunauer–Emmett–Teller analysis. Its catalytic activity was evaluated for Claisen–Schmidt condensation under solvent‐free conditions. The catalyst was easily recovered and reused up to five cycles without considerable loss of activity and was not deactivated due to amide formation. Also, this method has attractive advantages such as short reaction time, mild reaction conditions, good to excellent yield of products, easy handling of the catalyst and simple operational procedure. Copyright © 2014 John Wiley & Sons, Ltd.

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“…Different heterogeneous acid or basic catalysts have been employed to synthesize trans-chalcones, such as acid-clays [15], Bambo char sulfonic acid [9], potassium hydroxide impregnated silica gel [15], amino grafted zeolites [16], Amberlyst-15 and Amberlite-200C [17]. Silica-H2SO4 is a versatile, selective, and powerful catalyst that has been explored for various organic transformations, such as the synthesis of heterocyclic compounds [18], cross-aldol condensations [19], Michael additions [20], and oxidation reactions [21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chalcones via Claisen–schmidt Condensation Reaction Catalyzed by Silica-H2so4 Under Ultrasound Irradiation

Lahyani

Chtourou

Frikha

et al. 2014

JAC

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Solvent free synthesis of 1,3-diaryl-2-propenones catalyzed by commercial acid-clays under ultrasound irradiation

Cited by 40 publications

References 26 publications

Ultrasound-Assisted Syntheses of Chalcones: Experimental Design and Optimization

Ultrasound-Assisted Syntheses of Chalcones: Experimental Design and Optimization

Piperidine‐functionalized silica: an efficient and environmentally benign catalyst for Claisen–Schmidt condensation

Synthesis of Chalcones via Claisen–schmidt Condensation Reaction Catalyzed by Silica-H2so4 Under Ultrasound Irradiation

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