Green Synthesis and Biological Activity Investigation of New Thiazinotriazines: A Combined Experimental and Theoretical Investigation

Abstract

The Petasites hybridus rhizome water extract was used as a green media for the preparation of the Fe₃O₄/TiO₂/CuO@MWCNTs magnetic nanocomposites and its activity was evaluated by using it in the one-pot multicomponent reaction of isatoic anhydrides, electron deficient acetylenic compounds, α-haloketones, ammonium acetate, isothiocyanates and hydrazonoyl chloride in aqueous media at room temperature for the production of novel derivatives of thiazinotriazines in excellent yields. The synthesized thiazinotriazines have OH and NH functional groups that have acidic hydrogen and show high antioxidant activity. Moreover, reduction of organic pollutants such 4-nitrophenol (4-NP) was performed by synthesized Fe₃O₄/TiO₂/CuO@MWCNTs in water at room temperature. The outcomes showed this nanocatalyst was decreased organic pollutants in few seconds. Also, to better understanding reaction mechanism density functional theory based quantum chemical methods have been applied. The employed process for production of thiazinotriazines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products.

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:

• Diethyl oxalate
• thiazinotriazines
• six component reaction
• alkyl bromide
• anilines

Disclosure statement

No potential conflict of interest was reported by the authors.