Abstract
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.
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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