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Electrochemically induced oxidative cyclization of 2,3‐dihydroxypyridine. Synthesis of a novel highly oxygenated heterocyclic compound
Author(s) -
Varmaghani Fahimeh,
Nematollahi Davood
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1947
Subject(s) - chemistry , coulometry , cyclic voltammetry , aqueous solution , electrochemistry , glassy carbon , yield (engineering) , oxidative phosphorylation , electrode , organic chemistry , biochemistry , materials science , metallurgy
Electrochemical oxidation of 2,3‐dihydroxypyridine in aqueous phosphate buffer solution at a glassy carbon electrode has been studied using cyclic voltammetry and controlled potential coulometry. The results indicate that oxidation of 2,3‐dihydroxypyridine on glassy carbon electrode shows an irreversible feature in aqueous solution. This data indicates that the electrochemically generated pyridindione is unstable and via an oxidative conversion pathway converts to a novel highly oxygenated heterocyclic compound. By means of the obtained electrochemical data, an efficient, one‐pot method for the synthesis of this heterocyclic compound based on the oxidative cyclization of 2,3‐dihydroxypyridine under green conditions, and in a good yield and purity is described. Copyright © 2011 John Wiley & Sons, Ltd.