Magnetic nanoparticle supported amine: An efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation - 05/02/15

Doi : 10.1016/j.crci.2014.05.012

Anguo Ying ^a,^⁎ , Limin Wang ^a,^b, Fangli Qiu ^a, Huanan Hu ^a, Jianguo Yang ^a,^⁎
^a School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
^b Collegel of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China

^⁎Corresponding authors.

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Abstract

Amine functionalized silica coated Fe₃O₄ nanoparticles (SiO₂@MNP-A) were successfully prepared as a novel heterogeneous amine. The catalyst was characterized by XRD, FT-IR, TEM, magnetic measurement, elemental analysis and was found to be a magnetically separable and highly active catalyst for ambient Knoevenagel condensation of aromatic aldehydes and α-aromatic (heteroaromatic or polyaromatic)-substituted methylene compounds in water under ultrasonic irradiation to afford the corresponding products in good to excellent yields. Very interestingly, SiO₂@MNP-A successfully catalyze the reaction of the non-cyano substituted compound with benzaldehyde to achieve a key intermediate for the preparation of Atorvastatin calcium in green and atom-economic manner. In addition, the catalyst SiO₂@MNP-A can be reused for 8 times without any obvious loss of its activity. The role of ultrasonication in the Knoevenagel condensation was also discussed with the assistance of UV–vis spectrometry.

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Keywords : Magnetic nanoparticle, Immobilization, Ultrasonication, Knoevenagel condensation, Recyclability

Plan

Introduction

Results and discussion

Preparation and characterization of the catalyst (SiO₂@MNP-A)

SiO₂@MNP-A catalyzed Knoevenagel condensation of aromatic aldehydes and α-aryl -substituted methylene compounds in water under ultrasonic irradiation

Conclusions

Experimental

General

Preparation of silica coated magnetic nanoparticle (SiO₂@MNP)

Synthesis of the catalyst SiO₂@MNP-A

General procedure for the SiO₂@MNP-A catalyzed ambient Knoevenagel condensation in water under ultrasonic irradiation

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Vol 18 - N° 2

P. 223-232 - février 2015 Retour au numéro

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Magnetic nanoparticle supported amine: An efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation - 05/02/15

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