Amberlyst-15 and Amberlite-200C: Efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation

Lahyani, Achraf; Chtourou, Mohamed; Frikha, Mounir; Trabelsi, Mahmoud

doi:10.1016/j.ultsonch.2013.01.017

Cited by 27 publications

(28 citation statements)

References 34 publications

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“…Typical acid catalysts are AlCl 3 , RuCl 3 , silica-H 2 SO 4 , and TiO 2 /SO 4 2− [41, 42] whereas frequently used base catalysts include KOH, NaOH, K 2 CO 3 , Ba(OH) 2 , and MgO [43]. Heterogeneous Claisen–Schmidt condensation reactions are usually assisted by microwave [44] or ultrasound irradiation [45] to accelerate reaction rates or make the process environmentally more friendly. Recent reports have identified additional reactions that provide access to the chalcone scaffold, like the oxidation of alcohols [46], Meyer–Schuster rearrangement of propargylic alcohols [47], and Palladium-catalyzed carbonylative Heck reactions [48].…”

Section: Introductionmentioning

confidence: 99%

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

Hofmann

Webster

et al. 2016

Bioorganic & Medicinal Chemistry

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In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones’ effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.

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Section: Introductionmentioning

confidence: 99%

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

Hofmann

Webster

et al. 2016

Bioorganic & Medicinal Chemistry

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“…Cross-aldol condensation reaction between cycloalkanones and arylaldehydes has been used as the best synthetic route toward a,a 0 -bis(arylidene)cycloalkanones [29][30][31][32][33][34][35][36][37]. Several catalysts have been used to promote this transformation so far [29][30][31][32][33][34][35][36][37]. However, most of these methods are associated with one or more of the following disadvantages: (1) unwanted side-reactions, (2) need for application of sealed ampoules or tubes, (3) moderate yield, (4) long reaction time, (5) use of expensive, unavailable, and toxic catalysts, (6) application of additional energy (microwaves), (7) use of volatile organic solvents, (8) harsh conditions, and (9) poor agreement with green chemistry principles.…”

Section: Introductionmentioning

confidence: 99%

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

et al. 2016

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The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } was prepared by reaction of NEt 3 with ClSO 3 H and then with H 2 SO 4 . The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining a,a 0 -bis(arylidene)cycloalkanones in high yield after short reaction time. Graphical AbstractKeywords Protic acidic ionic liquid Á N,N-Diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } Á a,a 0 -Bis(arylidene)cycloalkanone Á Crossaldol condensation Á Solvent-free & Abdolkarim Zare

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“…Furthermore, at the best of our knowledge only a report exists for the synthesis of compounds 17 under heterogeneous conditions in a biphasic system H 2 O/dichlomethane, using NaOH as base in the presence of a phase transfer catalyst. 26 Thus, starting from that report, we developed a sustainable US-assisted method to obtain a new class of indanonylidenyl precursors of donepezil by substituting the homogeneous base catalyst with a commercial basic resin Amberlyst A-26 27 as efficient and recyclable heterogeneous catalyst to realize a regioselective aldol condensation between the indanones 5−9 and 1-benzyl-piperidine moieties 10−12.…”

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confidence: 99%

Design, Synthesis, and Evaluation of Donepezil-Like Compounds as AChE and BACE-1 Inhibitors

Costanzo

Cariati

Desiderio

et al. 2016

ACS Med. Chem. Lett.

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An ecofriendly synthetic pathway for the synthesis of donepezil precursors is described. Alternative energy sources were used for the total synthesis in order to improve yields, regioselectively, and rate of each synthetic step and to reduce the coproduction of waste at the same time. For all products, characterized by an improved structural rigidity respect to donepezil, the inhibitor activity on AChE, the selectivity vs BuChE, the side-activity on BACE-1, and the effect on SHSY-5Y neuroblastoma cells viability were tested. Two potential new lead compounds for a dual therapeutic strategy against Alzheimer's disease were envisaged.

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Amberlyst-15 and Amberlite-200C: Efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation

Cited by 27 publications

References 34 publications

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Design, Synthesis, and Evaluation of Donepezil-Like Compounds as AChE and BACE-1 Inhibitors

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