An efficient Knoevenagel condensation of aldehydes with active methylene compounds over novel, robust CeZrO4−δ catalyst

Sahani, Amber J.; Burange, Anand S.; Jayaram, Radha V.

doi:10.1007/s11164-018-3587-6

Cited by 9 publications

(2 citation statements)

References 37 publications

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“…Notably, for the synthesis of value-added chemicals, alkylation of active methylene compounds (AMCs) with olefins, benzyl halide, and condensation with carbonyl compound is regarded as one best way to construct C-C single and double bonds [4,5]. Though primarily for the activation of AMCs with various intermediates and unsaturated molecules like alkenes, [6] alkynes, [7][8][9], and 1, 3-dienes [8][9][10], different transition metal-based catalysts were carried out, remarkably, very few reports are available on the reaction of AMCs and various cyclic enol ethers (CEE) and acetal, excludes Knoevenagel condensation, alkylation on allylic alcohol/halide, and benzylic alcohols for the construct of a C-C bond [11][12][13][14][15][16][17]. For instance, Bihovsky et al used strong acid (trifluoroacetic acid) for the alkylation of CEE for condensing with the dicarbonyl compound through oxonium ion [18], whereas Nguyen et al reported alkylation of AMC on CEE using AuCl 3 -AgOTf catalysts [19].…”

Section: Introductionmentioning

confidence: 99%

Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds

2021

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In the present work, we report the catalytic reaction of active methylene compounds with cyclic enol ethers and aryl acetals through oxonium intermediate under solvent-free conditions using heterogeneous solid acid catalysts. Among studied solid acid catalysts, Amberlyst-15 gave excellent yields (35-85%) of alkylated products. The catalyst showed broader substrate scope, and a recyclable catalytic cost-efficient approach of the alkylation was examined on the different types of cyclic enol ethers and aryl acetal.

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Section: Introductionmentioning

confidence: 99%

Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds

2021

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“…Several strategies have been explored by this research group to accomplish the Knoevenagel condensation through a benign route. − A new strategy for the Knoevenagel condensation using magnesium oxide (MgO)-stabilized Pickering emulsion as PIC has been developed in the present study. MgO was prepared by precipitation and calcined at different temperatures.…”

Section: Introductionmentioning

confidence: 99%

Pickering Interfacial Catalysis—Knoevenagel Condensation in Magnesium Oxide-Stabilized Pickering Emulsion

2020

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In the present study, a novel catalytic route for the Knoevenagel condensation reaction has been developed by Pickering interfacial catalysis using magnesium oxide (MgO) as both an emulsion stabilizer and a base catalyst. MgO was prepared by the precipitation method using sodium hydroxide or ammonium hydroxide as the precipitating agent and calcined at different temperatures. The calcined samples were characterized by XRD, SEM, TEM, AFM, BET, and DLS techniques. The catalytic application of the emulsions stabilized by MgO was investigated for the Knoevenagel condensation reaction of benzaldehyde and its derivatives with malononitrile. All of the reactions were carried out at an ambient temperature (30 °C) under static conditions without stirring. Both the emulsion-stabilizing ability and the catalytic activity of MgO were found to be affected by the method of preparation, calcination temperature, and the nature of the oil phase. It was observed that the method of preparation varied the texture and morphology of MgO and thus the stability and droplet size of the emulsion formed. This was further reflected in the catalytic activity. The highest yield (87%) of the condensation product was obtained with MgO prepared by precipitation using a strong base (NaOH) and further calcined at 400 °C. The developed catalytic system offers several green chemistry advantages such as reusable solid-base catalyst and use of a single material as both emulsion stabilizer and catalyst. Room-temperature reaction under static conditions is an additional advantage of the developed catalytic system.

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Green synthesis of xanthene and acridine-based heterocycles of pharmaceutical importance: a review

Burange¹,

Gadam²,

Tugaonkar³

et al. 2021

Environ Chem Lett

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An efficient Knoevenagel condensation of aldehydes with active methylene compounds over novel, robust CeZrO4−δ catalyst

Cited by 9 publications

References 37 publications

Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds

Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds

Pickering Interfacial Catalysis—Knoevenagel Condensation in Magnesium Oxide-Stabilized Pickering Emulsion

Green synthesis of xanthene and acridine-based heterocycles of pharmaceutical importance: a review

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