Green Synthesis and Theoretical Study of New Azepinodiazepine Derivatives with Biological Activity: Application of Fe₃O₄/ZnO@MWCNT

Abstract

In this study, we synthesized azepinodiazepine derivatives in high yields using multicomponent reactions of isatins, activated acetylenic compounds, alkyl bromides, methyl aziridine and ammonium acetate in the presence of Fe₃O₄/ZnO@MWCNT as a high-performance catalyst and teiethyl amine in water at room temperature. The Fe₃O₄/ZnO@MWCNT synthesizes using Petasites hybridus rhizome water extract as a green media and moderate base. Also, the catalytic activity of the green synthesized Fe₃O₄/ZnO@MWCNT 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 a few seconds. Investigation of the antioxidant ability of synthesized compounds using radical trapping of diphenyl-picrylhydrazine (DPPH) and ferric reduction power experiment is another purpose of 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. Also, to better understanding reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. This procedure has some benefits such as short reaction time, products with excellent yields, simple catalyst and product separation.

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 solvents 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:

• Fe₃O₄/ZnO@MWCNTs MNCs
• azepinodiazepine derivative
• multicomponent reaction
• alkyl bromide
• isatin

Disclosure statement

No potential conflict of interest was reported by the author(s).