Zr-MOF-N=CH-C6H4-OSO3H Catalyst for the Construction of New Substituted 4-Aminocoumarin Analogs

Authors

• Masoumeh Goudarzvand Chegini ¹
• Masoud Mokhtary * ¹
• Afshin Pourahmad ¹

• Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.

Abstract

In this study, the preparation of a new functionalized acidic metal-organic framework nanocatalyst formulated as Zr-MOF-N=CH-C6H4-SO3H has been reported. After characterization using different analysis methods such as FT-IR, XRD, SEM, EDX, TGA, and TEM, the average size of the nanoparticles was found to be between 42.5 and 50.4 nm in diameter. The Nanocatalyst was utilized in the synthesis of novel substituted 4-aminocoumarin analogs via one-pot three-component reaction of 4-aminocoumarin, arylaldehyde or 3-(2-aryldiazenyl)-2-hydroxybenzaldehyde, and 6-hydroxyuracil or 1,3-dimethylbarbituric acid in good-to-excellent yields in ethanol at reflux conditions. A λmax of 362.7 nm was observed for compound 4e. Simple work-up of the process, mild reaction conditions, no by-products and easy reusability of the nanocatalyst are some of the advantages of the procedure.

Highlights 

·         A novel series of substituted 4-aminocoumarin analogs were synthesized.

·         A new functionalized acidic metal-organic framework catalyst Zr-MOF-N=CH-C₆H₄-OSO₃H was introduced.

·         High yields and easy work-up procedure are some advantages of this method.

·         A λ_max of 362.7 nm was observed for compound 4e.

·         The catalyst is easily recycled.

Graphical Abstract

Keywords

• Metal-organic framework
• Azo Dyes
• One-pot reaction.
• 4-Aminocoumarin
• Nanocatalyst