Abstract
Electrochemical oxidation of catechol ( 1a), 3-methylcatechol ( 1b), and 3-methoxycatechol ( 1c) has been studied in the presence of 4,6-dihydroxy-2-methylpyrimidine ( 3) as a nucleophile in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols ( 1a– 1c) participate in Michael addition reactions with 3 to form the corresponding benzofuro[2,3-d]pyrimidine derivatives ( 6a– 6c). The electrochemical synthesis of ( 6a– 6c) has been successfully performed in an undivided cell in good yield and purity. The mechanism of oxidation was deduced from voltammetric data and by coulometry at controlled-potential. The products have been characterized after purification by IR, 1H NMR, 13C NMR and MS.
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