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Electrochemical Oxidation of Catechols (=Benzene‐1,2‐diols) in the Presence of Benzoylacetonitrile: Synthesis of New Derivatives of 5,6‐Dihydroxybenzofuran
Author(s) -
Nematollahi Davood,
AtlasiPak Ali Reza,
Esmaili Roya
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200029
Subject(s) - chemistry , catechol , coulometry , cyclic voltammetry , electrochemistry , diol , benzene , nucleophile , organic chemistry , atom economy , medicinal chemistry , catalysis , electrode
The electrochemical oxidation of catechol (=benzene‐1,2‐diol; 1a ) and some of its derivatives in H 2 O/MeCN 1 : 1 containing benzoylacetonitrile (= β ‐oxobenzenepropanenitrile; 3 ) as a nucleophile was studied by cyclic voltammetry and controlled‐potential coulometry. The voltammetric data showed that electrochemically generated o ‐benzoquinones (=cyclohexa‐3,5‐diene‐1,2‐diones) from catechol ( 1a ) and 3‐methylcatechol ( 1b ) participate in a Michael ‐addition reaction with 3 to form the corresponding 5,6‐dihydroxybenzofuran‐3‐carbonitrile 8 ( Scheme 1 ). In this work, we report an efficient one‐pot method with high atom economy for the synthesis of new substituted 5,6‐dihydroxybenzofuran‐3‐carbonitriles in an undivided cell under ambient conditions.