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Updated: Jan 9, 2026

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
Published on: October 19, 2017
SnCl2-catalyzed Kabachnik-Fields synthesis of α-aminophosphonates with potent antioxidant activity
Achraf Hibot1,2, Salha Hamri2, Abderrafia Hafid2
1Laboratory of Medicinal Chemistry, Department of Pharmacology, Toxicology and Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, University of Barcelona Av. Joan XXIII, 27-31 Barcelona 08028 Spain mdpujol@ub.edu.
Abstract:
A novel and efficient method for synthesizing α-aminophosphonates was developed through a Kabachnik-Fields multicomponent reaction using 6-aminocoumarin or 6-aminobenzodioxane, benzaldehyde, triethyl phosphite, and a catalytic amount of SnCl2 in ethanol. The resulting 25 compounds 1a-l (71-92%) and 6a-m (45-96%) were obtained in moderate to excellent yields. Antioxidant activity, assessed via the FRAP and CUPRAC assays, the results demonstrated that several of these compounds exhibit comparable or even superior reducing power to ascorbic acid, particularly at low concentrations. These findings underscore the potential of these α-aminophosphonates as promising antioxidant agents for future applications. ADME analysis predicts good oral bioavailability, limited brain and skin penetration, and potential CYP450 inhibition.
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