Title:Bio-Fe3O4 Magnetic Nanoparticles Promoted Green Synthesis of thioxo- 1,3-Oxazole Derivatives: Study of Antimicrobial and Antioxidant Activity
Volume: 24
Issue: 8
Author(s): Maryam Ghazvini*, Fatemeh Sheikholeslami-Farahani*, Naghmeh Faal Hamedani, Ashraf Sadat Shahvelayati and Zohreh Rostami
Affiliation:
- Department of Chemistry, Payame Noor University(PNU), P.O. Box: 19395-4697, Tehran,Iran
- Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh,Iran
Keywords:
2-thioxo-1, 3-oxazole, Orange peel extract, Fe3O4-MNPs, Alkyl (aryl) isothiocyanates, Alkyl bromides, antioxidant
ability.
Abstract:
Aims and Objective: In this work, 1,3-oxazoles were generated using the
multicomponent reaction of α-bromo ketones, alkyl (aryl) isothiocyanates, sodium hydride and
Fe3O4 MNPs in the water at room temperature in good yields. The nanoparticles generated via the
biosynthesis method have potential value in different purposes, such as organic synthesis.
Materials and Methods: To study the antioxidant ability of some synthesized thioxo-1,3-oxazoles,
diphenyl-picrylhydrazine (DPPH) radical trapping and power of ferric reduction testes are
employed. Among the studied thioxo-1,3-oxazoles, compound 4b have good power for radical
trapping and reduction activity than the standard antioxidants such as BHT and TBHQ. In addition,
the antimicrobial activity of some thioxo-1,3-oxazoles was studied, employing the disk diffusion
test on Gram-positive bacteria and Gram-negative bacteria. The results of the disk diffusion test
showed that compounds 4a, 4b, 4d and 4f prevented bacterial growth.
Results: Without employing catalyst, these reactions have low yield and busy mixture. The
synthesis of compound 4a as sample reaction has a similar yield in the presence of ZnO-NPs and
Fe3O4 MNPs (entry 20 and entry 30), but the removal of catalyst from the mixture of reaction after
the completion of the reaction is comfortable in the presence of Fe3O4 MNPs. Structures of
compound 4a–4i are confirmed by IR, 1H NMR and 13C NMR mass spectra.
Conclusion: The reaction of α-bromo ketones, isothiocyanate and sodium hydride in the presence
of the catalytic amount of Fe3O4 MNPs in water generates 1,3-oxazole derivatives in good yields.
Some of the advantages of performing these reactions with the present procedure are to carry out
these reactions in water as a green solvent and simple removal of catalyst.
