Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

One-Pot Preparation of Various 2-Pyrazoles using Functionalized Fe Oxide Magnetic Nanoparticles with Sulfonated Tris(Hydroxymethyl)Aminomethane/Copper(II) Nitrate by in Situ Oxidation Method

Document Type : Research Article

Authors
Kaveh Khosravi
Amir Azizi
Fatemeh Karimi
Department of Chemistry, Faculty of Science, Arak University, Arak, I.R. IRAN
Abstract
In this research, first, functionalized Fe oxide magnetic nanoparticles based on sulfonated tris(hydroxymethyl)aminomethane/copper (II) nitrate were synthesized as a new, effective and recyclable magnetic catalyst, and then, was used in the reaction of preparing of Various 2-pyrazolines. Finally, the  prepared 2-pyrazolines were  oxidized to  the corresponding 2-pyrazoles under in situ and one-pot conditions, in such a way that, under optimal conditions, a wide and different range of unsaturated α, β-unsaturated  ketones (trans-chalcones) that had various functional groups including electron-donating and electron-withdrawing groups, were successfully transformed into the corresponding final products under easy and mild conditions. All products were obtained in good to excellent yields and no by-product was observed. The new synthesized magnetic nanocatalyst was characterized by various methods including infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy dispersive X-ray (EDAX), X-ray diffraction (XRD), elemental analysis (CHN) and analysis Thermogravimetry (TGA). The catalyst was easily recycled by the external magnetic field and was used for several times without observing a significant and effective decrease in its catalytic activity. Also, the structure of various synthesized 2-pyrazoles were confirmed by comparing their physical characteristics including melting point with the reported samples and also by infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectrum (1H-NMR), carbon nuclear magnetic resonance spectrum (13C-NMR) and elemental analysis. Finally, no using of harsh reaction conditions, the no by-product formation, as well as the ability to recycle and reuse the catalyst, made this method an environmentally friendly method.
Keywords
2-pyrazolines
2-pyrazoles α
β-unsaturated ketones
magnetic nanoparticles
tris(hydroxymethyl)aminomethan
copper (II) nitrate

Subjects

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