Synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1h-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives using an engineered copper-based nano-magnetic catalyst (Fe₃O₄@CQD@Si(OEt)(CH₂)₃NH@CC@Ad@Cu(OAc)₂)

Abstract

In this project, a novel magnetic nano catalyst was used in solvent-free conditions in three different experimental fabrication sections, including the synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives. Accordingly, in this study, a Carbon Quantum Dot (CQD)-based nanomagnetic catalyst (Fe₃O₄@CQD@Si(OEt)(CH₂)₃NH@CC@Ad@Cu(OAc)₂) was synthesized, in which the Fe₃O₄ nanoparticles surface was protected using carbon quantum dots (CQDs) instead of conventional SiO₂. The as-synthesized catalyst was characterized using different techniques, including Fourier transform infrared spectroscopy (FT-IR), X-ray powder Diffraction (XRD), Field Emission Scanning Electron Microscopy (FESEM), Transmission Electron Microscopy (TEM), Dynamic Light Scattering (DLS), Energy-Dispersive X-ray spectroscopy (EDX), EDX Elemental Mapping (EDX-Mapping), Thermal Gravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Vibrating Sample Magnetometer (VSM). The activity of the as-synthesized catalyst was evaluated in the synthesis of hexahydroquinolines, 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile and 1-aminoalkyl-2-naphthols derivatives. The solvent-free condition with low reaction time and high reaction yield is the results of the prepared catalyst. Moreover, the effect of temperature and the amount of the catalyst (optimum reaction condition) were determined using a systematic approach, namely, the Design of Experiment (DoE). How the reaction was triggered by the catalyst was determined by FT-IR analysis.

Graphical Abstract

Keywords:

• Carbon quantum dots (CQDs)
• Design of Experiment (DoE)
• hexahydroquinolines
• magnetic nano catalyst
• solvent-free reaction
• 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile
• 1-aminoalkyl-2-naphthols

Acknowledgements

The authors would like to appreciate the Research Council of Bu Ali Sina University for providing the facilities and financial support of this research.

Disclosure statement

No conflict of interest has been reported by the authors.