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Journal: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS) | Year:0 | Volume:8 | Issue:1 | Start Page:48 | End Page:58

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Title

A CONVERGENT PAIRED ELECTROCHEMICAL SYNTHESIS OF NEW HETEROCYCLIC COMPOUNDS. REACTION OF BENZOQUINONES WITH 3-AMINO-4-HYDROXYCOUMARIN

Writers

NEMATOLLAHI D. | KARBASI H.

Pages

 Start Page 48 | End Page 58

Abstract

 Electrochemical oxidation of CATECHOLs (1) has been studied in the presence of cathodically generated 3-AMINO-4- HYDROXYCOUMARIN (3a) as a nucleophile in aqueous solutions, using CYCLIC VOLTAMMETRY and controlled-potential coulometry. The results indicate that the o-benzoquinones derived from CATECHOLs (1) participate in Michael addition reaction with 3-AMINO-4- HYDROXYCOUMARIN (3a) to form the corresponding new heterocyclic compounds (7) (oxidized form of coumestan derivatives) . The electrochemical process consists of a multi-step including (a) cathodic reduction of 4-HYDROXY-3-NITROCOUMARIN (3) to 3-AMINO-4- HYDROXYCOUMARIN (3a), (b) anodic oxidation of CATECHOLs (1) to related o-benzoquinone (2), (c) the Michael addition reaction of 3- amino-4-hydroxycoumarin (3a) to o-benzoquinone (2), and (d) anodic oxidation of formed adduct. The PAIRED ELECTROCHEMICAL SYNTHESIS of compounds 7a and 7b has been successfully performed in a one-pot process at carbon rods as working and counter electrodes in an undivided cell.

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