Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity

Author(s): Roberta Bernini, Fernanda Crisante, Giancarlo Fabrizi, Patrizia Gentili

Journal Name: Current Organic Chemistry

Volume 16 , Issue 8 , 2012

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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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Article Details

Year: 2012
Published on: 04 April, 2012
Page: [1051 - 1057]
Pages: 7
DOI: 10.2174/138527212800194700
Price: $58

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