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Facile Chemoselective synthesis of 2‐(2‐(Methoxycarbonyl)‐3‐oxo‐2,3‐dihydrobenzofuran‐2‐yl)benzoic acids and 3 H ,3’ H ‐Spiro[benzofuran‐2,1′‐isobenzofuran]‐3,3′‐dione derivatives
Author(s) -
Firoozi Neda,
Roshan Zohreh,
Mohammadizadeh Mohammad Reza
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3963
Subject(s) - chemistry , isobenzofuran , benzofuran , acetic acid , benzoic acid , aqueous solution , ethanol , benzothiophene , organic chemistry , medicinal chemistry , stereochemistry , thiophene
Oxidation of some derivatives of 4b,9b–dihydroxyindeno[1,2‐ b ]benzofuran‐10‐one have been investigated in detail using lead(IV) acetate in acetic acid under reflux conditions and periodic acid in aqueous ethanol at room temperature. We realized that during the first 5–15 minutes of the oxidation reactions in lead(IV) acetate/acetic acid system, 3 H ,3’ H ‐spiro[benzofuran‐2,1′‐isobenzofuran]‐3,3′‐dione derivatives have been synthesized chemo selectively, while, if the reaction mixtures stirred for additional 3 hours, the main products would be 2‐(2‐(Methoxycarbonyl)‐3‐oxo‐2,3‐dihydrobenzofuran‐2‐yl)benzoic acids. Moreover, room temperature oxidation of 4b,9b–dihydroxyindeno[1,2‐ b ]benzofuran‐10‐ones by periodic acid (H 5 IO 6 ), leads to the formation of 3 H ,3’ H ‐spiro[benzofuran‐2,1′‐isobenzofuran]‐3,3′‐dione derivatives in good to excellent yields.