Gold Nanoparticle Functionalized Mesoporous Silica-Chitosan as Efficient and Recyclable Catalyst for the Green One-Pot Synthesis of 4H-pyran Derivatives in Aqueous Medium

Author(s): Razieh Azimi, Zahra Lasemi*, Ayemeh Bagheri Hashkavayi.

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 4 , 2020

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Abstract:

Gold nanoparticle functionalized mesoporous silica-chitosan (Au NPs/silica-chitosan) as an environmentally benign and heterogeneous nanocatalyst was prepared and its properties were characterized using field emission scanning electron microscopy (FE-SEM) and fourier transform infrared (FT-IR). The catalytic activity of Au NPs/silica-chitosan was studied in the synthesis of biologically important 4H-pyran derivatives. In these reactions, efficient and green syntheses of 4H-pyrans were carried out using isatins or aldehydes, active methylene compounds, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of Au NPs/silica-chitosan in water in excellent yields. Au NPs/silica-chitosan can be recovered easily and reused without any significant loss of the catalytic activity. 4H-pyran derivatives were synthesized using Au NPs/silica-chitosan as catalyst in three component reaction of isatins/aldehydes, active methylene, and 1,3-dicarbonyl compounds in water. Au NPs/Silica-Chitosan was prepared by reaction of aqueous solution of HAuCl4 (1 wt.%) and solution chitosan in deionized water and acetic acid with tetraethyl ortho silicate (TEOS) at 100ºC for 24 h. Gold nanoparticle functionalized mesoporous silica-chitosan was prepared and its catalytic activity was investigated for forming 4H-pyran derivatives. In this study, active methylene and 1,3-dicarbonyl compounds reacted with various isatins and aldehydes which afforded the corresponding spirooxindoles with 88-98% yields. This method includes the environmentally friendly reaction conditions, short reaction time, simple work-up, excellent yield, broad scope of usable substrates, recovery and reusability of heterogeneous catalyst.

Keywords: 4H-pyran, isatin, gold nanoparticle functionalized mesoporous silica-chitosan, 1, 3-dicarbonyl compound, reusable heterogeneous catalyst, catalytic activity.

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VOLUME: 17
ISSUE: 4
Year: 2020
Page: [268 - 280]
Pages: 13
DOI: 10.2174/1570178616666190618113635
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