Recyclable Keggin Heteropolyacids as an Environmentally Benign Catalyst for the Synthesis of New 2-Benzoylamino-N-phenyl-benzamide Derivatives under Microwave Irradiations at Solvent-Free Conditions and the Evaluation of Biological Activity

Molecules. 2017 Dec 21;23(1):8. doi: 10.3390/molecules23010008.

Abstract

2-Benzoylamino-N-phenyl-benzamide derivatives (5a-h) were prepared from 2-phenyl-3,1-(4H)-benzoxazin-4-one 3 and substituted anilines 4a-h in the presence of a Keggin-type heteropolyacids series (H₃PW12O40·13H₂O; H₄SiW12O40·13H₂O; H₄SiMo12O40·13H₂O; and H₃PMo12O40·13H₂O) as catalysts without solvent and under microwave irradiation. We found that the use of H₃PW12O40·13H₂O acid coupled to microwave irradiation allowed obtaining a high-yielding reaction with a short time. The compound structures were established by ¹H-NMR and 13C-NMR. The antibacterial and antifungal activities of the synthesized compounds exhibited an inhibition of the growth of bacteria and fungi.

Keywords: 2-benzoylamino-N-phenyl-benzamide derivatives; Keggin-type heteropolyacids; antibacterial; antifungal; microwave irradiation; solvent free conditions.

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Benzamides / chemical synthesis*
  • Catalysis
  • Magnetic Resonance Spectroscopy / methods
  • Microbial Sensitivity Tests
  • Microwaves*
  • Molecular Structure
  • Molybdenum / chemistry
  • Solvents / chemistry*
  • Structure-Activity Relationship
  • Tungsten Compounds / chemistry

Substances

  • Anti-Infective Agents
  • Benzamides
  • Solvents
  • Tungsten Compounds
  • Molybdenum