Ultrasound-promoted one-pot synthesis of α-aminophosphonates: X-ray crystallographic study and biological screening


Sehout I., Badaoui K., KÜÇÜKBAY H., Nemouchi S., Bendjeddou L., Bensouici C., ...More

Phosphorus, Sulfur and Silicon and the Related Elements, vol.201, no.1, pp.96-109, 2026 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 201 Issue: 1
  • Publication Date: 2026
  • Doi Number: 10.1080/10426507.2025.2584184
  • Journal Name: Phosphorus, Sulfur and Silicon and the Related Elements
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core
  • Page Numbers: pp.96-109
  • Keywords: antifungal activity, antioxidant activity, crystal structure, ultrasound-assisted synthesis, α-aminophosphonates
  • Inonu University Affiliated: Yes

Abstract

A green and efficient approach was developed for the synthesis of twenty-three α-aminophosphonate derivatives (4a-4v) via the Kabachnik–Fields reaction, using acetylsalicylic acid as a novel eco-friendly Brønsted acid catalyst under ultrasound irradiation and solvent-free conditions. The target compounds were obtained in moderate to excellent yields (43 - 91%) and were structurally characterized by FTIR, 1H NMR, 13C NMR, and single-crystal X-ray diffraction analysis. Notably, the crystal structure of compound 4c was elucidated by X-ray diffraction, providing detailed molecular and supramolecular insights. The antioxidant activity of the synthesized compounds was evaluated through four in vitro assays (DPPH, ABTS, FRAP, and phenanthroline), with compounds 4a, 4c, 4d, and 4k demonstrating significant potency. Additionally, antifungal activity was assessed against Fusarium oxysporum f. sp. lycopersici, with compound 4t exhibiting the highest inhibitory effect.