Synthesis of 3-[4-({Methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl}amino)-1,3-thiazol-2-yl]-2-aryl-1,3-thiazolan-4-ones as Potential Biodynamic Agents

Abstract

A series of isoxazolyl thiazolyl thiazolidinones ( 4a–h ) were synthesized starting from isoxazolyl chloroacetamide 1 . Compound 1 upon heating with thiourea in ethanol furnished N4-{3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl]-1,3-thiazole-2,4-diamine 2 . Condensation of 2 with aromatic aldehydes afforded corresponding Schiff bases ( 3a–h ), which undergo cyclocondensation on treatment with mercaptoacetic acid to give 3-[4-({methyl-5-(E)-2-phenyl-1-ethenyl]-4-isoxazolyl] amino)-1,3-thiazol-2-yl]-2-aryl-1, 3-thiazolyl –4-ones ( 4a–h ) in excellent yields. Structures of all the synthesized compounds have been established by elemental analyses, IR, ¹H NMR, and mass spectral data.

Keywords:

• Isoxazolyl thiazoles
• isoxazolyl thiazolyl Schiff bases
• isoxazolyl thiazolyl thiazolidinones

Notes

∗Compounds (3a–h) were purified by column chromatography.

∗Compounds (4a–h) were purified by column chromatography.