Novel Mannich bases bearing pyrazolone moiety. Synthesis, characterization and electrochemical studies

Abstract

The present investigation describes a series of new {4-[3-Methyl-5-oxo-4-(4|-substituted phenyl hydrazono)-4,5-dihydro-pyrazol-1-yl]-phenoxy}-acetic acid (2-oxo-1-piperidine-1-ylmethyl-1,2-dihydro–indol-3-ylidene)-hydrazides synthesized by the Mannich reaction of {4-[3-Methyl-5-oxo-4-(4|-substituted phenyl hydrazono)-4,5-dihydro-pyrazol-1-yl]-phenoxy}-acetic acid (2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazide with aqueous formaldehyde and a solution of piperidine in dimethylformamide. These novel Mannich bases were characterized by elemental analysis, IR, 1H NMR and mass spectral data. Electrochemical behavior of these compounds were studied by two techniques namely polarography and cyclic voltammetry. The results from both the techniques were compared and the reduction mechanism in acidic as well as basic medium was proposed.

Keywords

• Mannich bases
• synthesis
• polarography
• cyclic voltammetry
• comparison
• reduction mechanism