Synthesis and Characterization New Schiff Bases,Pyrazole and Pyrazoline Compounds Derived From Acid Hydrazide Containing Isoxazoline Ring

Abstract

The work involves synthesis of new Schiff bases ( [V]a, b and [VI]a, b), pyrazoles[VII]a, b and pyrazolines[VIII]a, b derivatives containing isoxazoline unit starting with chalcones. 4bromoacetophenone was reacted with 4-hydroxybenzaldehyde or 4-hydroxyacetophenone was reacted with 4-bromobenzaldehyde in basic medium to give chalcone by Claisen-Schemidt reaction. The chalcons [I]a, b was reacted with hydroxylamine hydrochloride to form  isoxazolines [II]a, b. which were reacted with ethyl chloro acetate in basic medium to get ester compounds[III]a, b .The condensation new ester[III]a, b with hydrazine hydrate80% yieldedacid hydrazide [IV]a, b.The later compound refluxing  with  4-substituted benzaldehyde in dry benzene to give Schiff bases([V]a, band [VI]a, b)while the reaction of acid hydrazide [IV]a, b with acetylacetone or ethyl aceto acetate to get pyrazole[VII]a, b , pyrazolone[VIII]a, b ,respectively.The synthesized compounds were characterized by melting points, FTIR, mass and 1H NMR spectroscopy(of someof them).