A Facile Synthesis of Some Bioactive Isoxazoline Dicarboxylic Acids via Microwave-Assisted 1,3-Dipolar Cycloaddition Reaction

Abstract

The microwave-assisted 1,3-dipolar cycloaddition reaction of several aldoximes and dimethyl-2-methylene glutarate in the presence of diacetoxyiodobenzene as an oxidant produced four new isoxazoline-derived dimethyl carboxylates. Saponification followed by acidification of the latter yielded novel isoxazoline dicarboxylic acids in reasonable to high yields. The structures of these novel compounds were characterized by IR, 1H-NMR, 13C-NMR, and HRMS spectroscopy. Their biological activities disclosed higher inhibition of the growth of E. coli organisms by the aromatic compounds than by the aliphatic derivatives, demonstrating their potential in antibiotics research.

Keywords

• microwave-assisted 1,3-dipolar cycloaddition reaction
• isoxazoline
• antibiotics
• saponofication