Synthesis and characterization of new (Bis) Schiff base derivatives based on adamantane and evaluation antioxidant activity

In this study, we synthesized a series of new Schiff base derivatives containing adamantane moiety in the skeleton structure using adamantanol as the initial material, the adamantanol undergoes two reaction steps. In the first step, adamantanol reacts with acetanilide to produce 1,3-bis(4-acetamido-1-phenyl)adamantane as a salt. In the second step, the produced salt prepared in first step undergoes de-protection reaction by react with aqueous solution of sodium hydroxide to generate 1,3-bis (4-amino-phenyl)adamantane. This amine derivative reacts with different aromatic aldehydes to synthesis Schiff base derivatives of adamantane, as well as characterization of hybrid compounds by FT-IR, Mass spectroscopy, 1H-NMR, 13C-NMR, and study of antioxidant activity. All synthesized derivatives have good scavenging ability against (2,2 diphenyl-1-picrylhydrazyl) free radical, at the range of 81.4-89.9% at high concentration of 1 mg/mL.