Several 1-aryl-hydroxy and dihydroxyisochromans were synthesized by a two-steps procedure based on the oxa-Pictet-
Spengler reaction performed for the first time in dimethyl carbonate (DMC) from phenethyl alcohols and substituted benzaldehydes followed
by the regioselective aromatic hydroxylation/oxidative aromatic demethylation with 2-iodoxybenzoic acid (IBX)/sodium dithionite
(Na2S2O4) system. Some of them showed a novel pattern of hydroxylation degree into A ring. All synthesized isochromans were tested
about their radical scavenging activity by 2,2-diphenyl-2-picrylhydrazyl radical (DPPH.) method. Experimental results showed that dihydroxyisochromans
were more active than the corresponding phenolic or guaiacolic parent compounds confirming the key role of the
catecholic moiety for the antioxidant activity.
Keywords: Antioxidants, 1-aryl-dihydroxyisochromans, Aromatic hydroxylation, Catecholic compounds, Dimethyl carbonate (DMC), DPPH
radical assay, 2-iodoxybenzoic acid (IBX), oxa-Pictet-Spengler reaction.
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