Synthesis of novel biaryl derivatives of sesamol (5-Benzodioxolol) and evaluation of their antioxidant activity against DPPH radical

Abstract

A simple and direct arylation of sesamol with aryl halides by a photoinduced reaction is reported. Five 6-arylsesamol derivatives were synthesized in order to evaluate possible changes in their antioxidant properties as a function of the C6 aryl substituent nature. Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring-closure products bearing a tetracyclic aromatic condensed ring system, although in lower overall yields (~45 %). The antioxidant activity of the synthetic derivatives towards 1,1-diphenyl-2-picrylhydrazyl radical was determined taking sesamol as the reference compound. In addition, the relationship between the antiradical activities of these molecules against this radical and the bond dissociation energies of their phenolic O–H group was calculated using computational chemistry methods.