Synthesis of novel benzopyrimido[4,5-d]azoninone analogs catalyzed by biosynthesized Ag-TiO2 core/shell magnetic nanocatalyst and assessment of their antioxidant activity

Abstract

The present work reported the synthesis of novel benzopyrimido[4,5-d]azoninone analogs using a biosynthesized Ag-TiO₂ core/shell magnetic nanocatalyst. Accordingly, three-component one-pot reactions of benzoazonine-dione with thiourea and aryl aldehyde derivatives under nanocatalytic and optimized conditions afforded reasonable to brilliant yields of the target products (57–91%). The nanocatalyst was synthesized by a facile method using turmeric ethanol extract as a reducing and chelating agent. The synthesized nanocatalyst was verified by FT-IR, XRD, zeta potential, EDX, SEM, and TEM. The nanocatalyst presented remarkable catalytic activity for the synthesis of the target products. The procedure provided biosynthesis of the nanocatalyst, accessible reagents, high yields and rates of the reactions, nanocatalyst recyclability, and ease of product isolation and purification. The novel products were characterized by FT-IR, ¹H-NMR, ¹³C-NMR, mass spectra, and 2D NMR analysis (COSY, NOESY, HMQC & HSQC) spectral analyses. The antioxidant activity was assessed by DPPH and phosphomolybdate assays, in which the compounds exhibited excellent potency. Overall, this approach could be used to develop new and sustainable methods for the synthesis of antioxidants and other biologically active molecules.