The Synthesis and characterization of N-((3-(2, 4-dimethylphenyl)isoxazol-5-yl-methyl)cyclohexanamine

Isoxazole derivatives have been used a key intermediates in synthesis and have been investigated intensively for the last several years because of their biological activities [1]. In spite of this wide spectrum of properties, the number of isoxazoles tri-substituted by different functional groups, useful as scaffolds in the synthesis of many differently tri-substituted isoxazole, is scarce [2]. This research work describes the synthesis of new compound of isoxazole family. First, 2, 4-dimethylbenzaldehyde (1) was transformed to 2, 4-dimethylbenzaldoxime (2) by using NH2OH in pyridine. The in situ generated nitriloxide from reaction between (2) and NaOCl, was reacted with propargylalcohol to produce 3-(2, 4-dimethylphenyl)-5-hydroxymethyl isoxazole (3) in a cycloaddition procedure. Then, bromination of compound (3) with PBr3 in CH2Cl2, to produced 3-(2, 4-methylphenyl)-5-bromomethyl isoxazole (4). The final compound were synthesized by reaction of Et 3 N and cyclohexylamine with compound (4) in presence of benzene, to produce N-((3-(2, 4-dimethylphenyl)isoxazol-5-yl-methyl)cyclohexanamine The structure of all the synthesized compounds were characterized and confirmed by FT-IR and NMR spectroscopy techniques.