Efficient One-pot microwave-assisted Synthesis and Spectroscopic Characterization of Novel Antitumor and Antimicrobial Hydroxypyrrolidin2-ones

Mohamed Azmy, Eman Azmy; Awad, Boshra M.; Hefni, Halima A.; Saad, Hanaa A.; Eltoukhy, Affaf M.; Mabied, Ahmed. F.

doi:10.21608/jsrs.2018.25663

Efficient One-pot microwave-assisted Synthesis and Spectroscopic Characterization of Novel Antitumor and Antimicrobial Hydroxypyrrolidin2-ones

Document Type : Original Article

Authors

¹ chemistry, faculty of women, ain shams university, cairo, egypt

² Department of Chemistry, Faculty of Women for Arts, Science, and Education, Ain Shams University, Heliopolis, Cairo, Egypt

³ X-Ray Crystallography Lab., Solid State Physics Department, National Research Centre, Dokki, Giza, Egypt

10.21608/jsrs.2018.25663

Abstract

A microwave-assisted, chemoselective synthesis of the novel antitumor and antimicrobial (3E)-5-hydroxy-1-isopropyl-3-[(5-methyl-2-thienyl)methylene]-5-phenylpyrrolidin-2-one has been achieved via assisted microwave solvent-free one-pot reaction of (3E)-3-[(5-methyl-2-thienyl)methylene]-5-phenylfuran-2(3H)-one with amines, urea and thiourea. The products are obtained in significant purity, yield, and eco-friendly reaction conditions. The structural formula of the products is confirmed by their spectroscopic characterizations. A mechanism is proposed in which an intramolecular nucleophilic attack takes place on the carbonyl carbon by the lone pair of electrons on the nitrogen atom, leading to ring closure with proton transfer to oxygen forming the hydroxyl group.

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