Abstract
In this work, l-tryptophan functionalized silica-coated magnetic nanoparticles were readily prepared and evaluated as a recyclable magnetic nanocatalyst for the synthesis of spiro[indene-2,2′-naphthalene]-4′-carbonitrile derivatives through the one-pot four-component reaction of malononitrile, cyclohexanone, aromatic aldehydes, and 1,3-indandione. This novel magnetic nanocatalyst was confirmed to be effective and provide products in moderate to excellent yields under reflux conditions. The structure of obtained nanoparticles was characterized using FT-IR, XRD, VSM, EDX, elemental mapping, FE-SEM, and TGA. This synthetic protocol provides several benefits such as excellent yields in short reaction times (64–91%), saving costs, reusability of the catalyst using an external magnet (seven runs), and low catalyst loading.
Highlights
Multicomponent reactions (MCRs) and associated one-pot synthesis such as domino, tandem and cascade reactions have always been one of the most signi cant scopes in the development of new methodologies in organic synthesis and catalysis due to their great applications, in pharmaceutical studies.[1,2,3,4]
When the reaction was carried out using Fe3O4@SiO2-L-tryptophan NPs as the catalyst in EtOH, the product was obtained in excellent yields in a very short time (Table 1, entry 7)
The resulting Magnetic nanoparticles (MNPs) were collected by magnetic separation followed by washing with ethanol and water several times before being dried in an oven at 60 C to give Fe3O4@SiO2@L-tryptophan as a light brown powder
Summary
Multicomponent reactions (MCRs) and associated one-pot synthesis such as domino, tandem and cascade reactions have always been one of the most signi cant scopes in the development of new methodologies in organic synthesis and catalysis due to their great applications, in pharmaceutical studies.[1,2,3,4] MCRs o en produce highly complex molecules from simple precursors, avoiding complicated puri cation steps and saving solvents, reagents and times.[5,6,7]. We introduce a straightforward approach for the fabrication of Fe3O4@SiO2-L-tryptophan as a robust inorganic-organic hybrid catalyst This heterogeneous, environmentally benign, and highly reusable catalyst represents high catalytic activity to synthesize spiro[indene-2,20-naphthalene]-40-carbonitrile derivatives via a one-pot, four-component condensation reaction of malononitrile (1 mmol), cyclohexanone (1 mmol), various aromatic aldehydes (1 mmol) and 1,3indandione (1 mmol) under re ux conditions in EtOH. When the reaction was carried out using Fe3O4@SiO2-L-tryptophan NPs as the catalyst in EtOH, the product was obtained in excellent yields in a very short time (Table 1, entry 7). We have investigated the retrievability of Fe3O4@SiO2-L-tryptophan MNPs using the model reaction of malononitrile, cyclohexanone, 4-nitro benzaldehyde, and 1,3indandione
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