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.
Current Organic Chemistry
Title:Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity
Volume: 16 Issue: 8
Author(s): Roberta Bernini, Fernanda Crisante, Giancarlo Fabrizi and Patrizia Gentili
Affiliation:
Keywords: Antioxidants, 1-aryl-dihydroxyisochromans, Aromatic hydroxylation, Catecholic compounds, Dimethyl carbonate (DMC), DPPH radical assay, 2-iodoxybenzoic acid (IBX), oxa-Pictet-Spengler reaction.
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.
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Cite this article as:
Bernini Roberta, Crisante Fernanda, Fabrizi Giancarlo and Gentili Patrizia, Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity, Current Organic Chemistry 2012; 16 (8) . https://dx.doi.org/10.2174/138527212800194700
DOI https://dx.doi.org/10.2174/138527212800194700 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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