Synthesis of polyhydroquinolines and propargylamines through one-pot multicomponent reactions using an acidic ionic liquid immobilized onto magnetic Fe3O4 as an efficient heterogeneous catalyst under solvent-free sonication

As a continuation of previous work involving the application of Lewis acidic ionic liquids supported onto magnetic nanoparticles in organic synthesis,65 we report the use of the material as a recyclable catalyst for multicomponent reactions in the synthesis of polyhydroquinolines through Hantzsch condensation and propargylamines through A3-coupling reaction under solvent-free sonication

Hai Truong Nguyen; Vy Anh Truong; Phuong Hoang Tran

2020

Scholarcy highlights

  • The application of heterogeneous catalysts in organic synthesis has attracted much attention due to the prominent features of these catalysts, such as high efficiency, simple recovery, and reusability. the major limitation of heterogeneous catalysts is their low catalytic activity and selectivity because of slow dispersibility in the solvent. Magnetic nanoparticles are known as a new type of catalyst support because of their easy synthesis, good stability, high surface area, and facile separation from the reaction mixture. Currently, there are many reports about the catalytic performance of Fe3O4@ZrO2/ SO42ÀMNPs, Fe3O4@SiO2–SO3H MNPs, CoFe2O4@SiO2– SO3H MNPs, Fe3O4@ ZrO2–Pr–SO3H MNPs, and CuFe2O4 @SO3H MNPs9 in organic synthesis
  • Lewis acidic ionic liquids supported on magnetic nanoparticles have been extensively studied in organic synthesis due to high efficiency, simple recovery by an external magnet, excellent thermal stability, and reuse without loss of the activity
  • As a continuation of previous work involving the application of Lewis acidic ionic liquids supported onto magnetic nanoparticles in organic synthesis, we report the use of the material as a recyclable catalyst for multicomponent reactions in the synthesis of polyhydroquinolines through Hantzsch condensation and propargylamines through A3-coupling reaction under solvent-free sonication
  • MNPs were obtained by a simple co-precipitation method in the presence of KOH solution
  • The catalytic activity of LAIL@MNP was demonstrated through a one-pot multicomponent reaction of phenylacetylene, piperidine, and aldehydes under solvent-free sonication
  • The zinc species of LAIL@MNP catalyst coordinated with oxygen on the carbonyl group of benzaldehyde, which enhanced the electrophilicity of carbonyl carbon, providing rise to a better nucleophilic attack of piperidine to benzaldehyde to produce intermediate products
  • The LAIL@Magnetic nanoparticles can be quickly recovered and reused without a considerable decline in catalytic activity

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