Diastereoselective Synthesis of Trans-1H-Chromeno[2,3-d]Pyrimidine-2,4,6(3H)-Trione Derivatives by KF/Stilbite Zeolite NPs as a Novel Heterogeneous Nanocatalyst and Evaluation of Their Antimicrobial and Antioxidant Activity

Abstract

A green protocol for diastereoselective synthesis of trans-trans-1H-Chromeno[2,3-d]pyrimidine-2,4,6(3H)-trione was applied by tandem aldol-Michael reactions between 1,3-dimethylbarbituric acid, aldehydes, and dimedone at room temperature on the water as well as the present of KF/Stilbite nanoparticles. Also, the catalytic activity of the nanocatalyst (NC) was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the NCs have very high and effective catalytic activity for organic pollutants within a few seconds. Antioxidant abilities of synthesized compounds were revealed using radical trapping of diphenyl-picrylhydrazine (DPPH) and ferric reduction power experiments. The compounds 4a–d had excellent DPPH^• radical scavenging. Also, the antimicrobial activity of some synthesized compounds was proved by employing the disk diffusion test on Gram-positive and Gram-negative bacteria.

HIGHLIGHTS

• Synthesis of diastereomer derivatives is important in medicinal chemistry. This research was designed for easy synthesis of diastereoisomer derivatives of 1H-chromeno[2,3-d]pyrimidine-2,4,6(3H)-triones.

• The heterocyclic compounds have a recognized subject due to having a wide range of medicinal properties. The synthesized compounds revealed biological activities.

• Zeolites have cation replacement. Stilbite (ST), a natural zeolite with a framework structure and high internal surface area, is more effective because of its exchange capability for cations particularly for Na⁺ and Ca²⁺. Therefore, stilbite was used as a catalyst.

Graphical Abstract

Keywords:

• KF/Stilbite
• nanocatalyst
• 1H-chromeno
• antioxidant activity
• antimicrobial activity
• organic pollutants

Acknowledgment

The authors gratefully acknowledge the Islamic Azad University of Gorgan for spiritual support.

Disclosure statement

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