One-pot three-component synthesis of some new azo-pyrazoline derivatives

Abstract

The starting material azo-benzyloxy acetophenone (2) has been synthesized in three steps; the direct diazotization of p-aminoacetophenone and its coupling reaction with m-cresol gave azo-acetophenone (1), which was benzylated with p-chlorobenzylchloride to give the starting material (2). The later compound was subjected to the one-pot three-component condensation reaction with substituted benzaldehydes and phenylhydrazine in the presence of sodium hydroxide to afford the target molecule azo-pyrazoline derivatives (3a-e) in high yields and short reaction times. The structures of the synthesized compounds were elucidated by using FT-IR, ¹H NMR, ¹³C NMR and ¹³C DEPT 135 spectra.