Synthesis and Investigation of Biological Activity of New Oxazinoazepines: Application of Fe₃O₄/CuO/ZnO@MWCNT Magnetic Nanocomposite in Reduction of 4-Nitrophenol in Water

Abstract

In this study, oxazinoazepine derivatives were synthesized in high yields using multicomponent reactions of aniline, oxalylchloride, alkyl bromides, activated acetylenic compounds, ethyl glycinate, and methyl epoxide in the presence of Fe₃O₄/CuO/ZnO@MWCNT as a high-performance catalyst in water at room temperature. The Fe₃O₄/CuO/ZnO@MWCNT was synthesized using Petasites hybridus rhizome water extract as a green media and moderate base. Also, the catalytic activity of the green synthesized Fe₃O₄/CuO/ZnO@MWCNT magnetic nanocomposits (MNCs) was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized NCs have very high and effective catalytic activity for organic pollutants within few seconds. Investigation of antioxidant ability of synthesized compounds using radical trapping of diphenyl-picrylhydrazine (DPPH) and ferric reduction power experiment is another purpose in this research. Also, the antimicrobial activity of some synthesized compounds was proved by employing the disk diffusion test on Gram-positive and Gram-negative bacteria. This procedure has some benefits such as short reaction time, product with excellent yields, simple catalyst, and products separation.

Graphical Abstract

Highlights

• Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication, and applications of chemical products. Among solvents, water is a green solvent and very suitable for performing organic reaction.

• The present procedure avoids the use of toxic solvent.

• Some representatives of this class of azaheterocycles are known as antiviral agents, glycosidase inhibitors, anticancer agents or antidiabetics. Therefore, in view of their medicinal relevance, an increasing number of synthetic methods have been described in recent years for the construction of highly substituted azepine derivatives.

Keywords:

• Alkyl bromide
• Fe₃O₄/CuO/ZnO@MWCNTs magnetic nanocomposits (MNCs)
• isatins
• oxazinoazepine derivatives
• six component reaction

Acknowledgement

We gratefully acknowledge from Islamic Azad University of Karaj because of spiritual support.

Disclosure statement

No potential conflict of interest was reported by the authors.