A silver nanoparticles-catalyzed efficient three-component synthesis of polysubstituted 4H-chromenylphosphonates and their antioxidant activity

Abstract

A simple and efficient protocol for one-pot three-component synthesis of structurally diverse dialkyl 2-amino-3-cyano-4H-chromen-4-ylphosphonates from the condensation of salicylaldehydes, malononitrile, and trialkyl phosphite using silver nanoparticles as catalyst in ethanol at reflux has been developed. Selected new compounds were evaluated for their antioxidant activity by free radical screening using 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. Among the compounds employed, 5a, 5 b, and 5 h showed promising DPPH radical scavenging activities compared to the experimental standards at low concentration (100 µg/mL) after 24 h incubation.

Graphical Abstract

Keywords:

• Antioxidant activity
• dialkyl 2-amino-3-cyano-4H-chromen-4-ylphosphonates
• multicomponent reaction
• nanocatalyst
• silver nanoparticles

Additional information

Funding

We thank the Ministry of Higher Education and Scientific Research (Algeria), and Abant Izzet Baysal Ûniversitesi, BAP Commission (BAP grant No. 2016.03.03.1071 and 2014.03.03.761) for the financial supports.