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- Title
New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst.
- Authors
Ghavidel, Hassan; Mirza, Behrooz; Soleimani‐Amiri, Somayeh; Manafi, Mohammadreza
- Abstract
A green synthesis of functionalized 4H‐chromenes using one‐pot, three‐component reaction of salicylaldehyde (1), active methylene (2), and carbon‐based nucleophile (3) using Fe3O4@CONa nanoparticles in water has been performed at 60°C. The Fe3O4@CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst and solvent, short reaction time, high product yields, as well as simple work‐up procedure were found as some advantages of this methodology. The density functional theory calculations were applied to all‐inclusive perception of the one‐pot, three‐component reaction mechanism. The most reactions progressed through the following route: (a) nucleophilic addition of 2 to 1; (b) ring closing, dehydration; (c) nucleophilic substitution of 3 (2‐naphtol, 4‐hydroxycumarin) to intermediate. Sometimes mechanism mutated to: (a) nucleophilic addition of 3 (indole, 2‐methylindole) to 1, and dehydration; (b) nucleophilic addition of 2 to intermediate; and (c) ring closing, and dehydration. The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms. Theoretical study could be so helpful to pick out suitable reactants of the reaction. Density functional theory (DFT) calculations were applied to study of the one‐pot, three‐component synthesis of functionalized 4H‐chromenes in basic medium.DFT study identified two various mechanisms due to different reactants.The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms.Theoretical study helped to choose suitable reactants of salicylaldehyde (1), active methylene (2), and carbon‐based nucleophile (3).The Fe3O4@CONa nanoparticle was synthesized and applied as an efficient, green, and magnetically reusable heterogeneous catalyst in the reaction.Green synthesis of functionalized 4H‐chromenes performed using Fe3O4@CONa nanoparticles in water at 60°C.
- Subjects
MAGNETIC nanoparticles; FRONTIER orbitals; CATALYSTS; DENSITY functional theory; ELECTRIC potential; HETEROGENEOUS catalysts; INDOLE
- Publication
Journal of the Chinese Chemical Society, 2020, Vol 67, Issue 10, p1856
- ISSN
0009-4536
- Publication type
Article
- DOI
10.1002/jccs.201900554