Chemical Review and Letters

Design of functionalized ferrite Nano Magnetic Catalyst (Fe3O4@SiO2/Si(CH2)3NH/HMPO/Pd(OAc(Fe3O4@SiO2/Si(CH2)3NH/HMPO/Pd(OAc)2) for the synthesis of benzo[a]xanthen-11-one and chromeno[2,3-b]pyridine-3-carbonitrile derivatives and biological studies

Document Type : Research Article

Authors

Mohammad Reza Poor Heravi 1
Mehdi Lashgari 1
Bagher Mohammadi 1, 2

1 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697 Tehran, Iran

2 Department of Chemistry, University of Zanjan, Zanjan, 45371-38791, Iran

https://doi.org/10.22034/crl.2024.460647.1345
Abstract
In the present study, a novel magnetic organosilica supported Pd-Schiff base complex (Fe3O4@SiO2/Si(CH2)3NH/HMPO/Pd(OAc)2) was prepared. The nanocatalyst were synthesized using Fe3O4@SiO2 core–shell nanoparticles and functionalized with 3-chloropropyltrimethoxysilane (CPTMS) as Fe3O4@SiO2@Cl. The Schiff base ligand was synthesized by reaction of 5-hydroxypicolinaldehyde with hydrazine to produce of (hydrazineylidenemethyl)pyridin-3-ol (HMPO), then palladium acetate was added to produce of Schiff-base-Pd(II) complex. The catalyst was characterized thoroughly by FT‐IR, XRD, SEM, TEM, VSM, EDX, TGA, SEM image of elemental maps and ICP analyses. Its catalytic activity was assessed in the synthesis of 12-aryl- 8,9,10,12-tetrahydrobenzo[a]xanthenes-11-one, 14-aryl-14H- hexahydro-11H-benzo[a]xanthen-11-one and chromeno[2,3-b]pyridine-3-carbonitrile derivatives through a one-pot condensation of dimedone or malononitrile, naphthols, and aryl aldehydes in EtOH/H2O.The reaction involves formation of C-C, C-O and C-N bonds from readily available starting materials via a domino multicomponent strategy in the absence of Nano Cat by scan of solvents, amount of nanocatalyst(10 mol%), in a single synthetic operation. Reusability of nanocatalyst (4) in the synthesis of compound 13n, 14j is five times. Products of (13a-n), and (14a-j) antibacterial activity were evaluated against 10 type of organism and show good results. The excellent yield of products, easy work-up, column-free, short reaction time, and facility of reusability by an external magnet are other important advantages of this methodology.

Graphical Abstract

Design of functionalized ferrite Nano Magnetic Catalyst (Fe3O4@SiO2/Si(CH2)3NH/HMPO/Pd(OAc(Fe3O4@SiO2/Si(CH2)3NH/HMPO/Pd(OAc)2) for the synthesis of benzo[a]xanthen-11-one and chromeno[2,3-b]pyridine-3-carbonitrile derivatives and biological studies

Keywords

Tetrahydrobenzo[a]xanthene
Chromeno[2,3-b]pyridine-3-carbonitrile
Heterogeneous catalyst
MNPs
Schiff-base-Pd(II) complex

Subjects

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Chemical Review and Letters
Volume 7, Issue 4 - Serial Number 4
September and October 2024
Pages 597-621

  • Receive Date 02 June 2024
  • Revise Date 28 August 2024
  • Accept Date 30 August 2024

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