Paper Information

Journal:   JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)   MARCH 2011 , Volume 8 , Number 1; Page(s) 48 To 58.
 
Paper: 

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

 
 
Author(s):  NEMATOLLAHI D.*, KARBASI H.
 
* FACULTY OF CHEMISTRY, BU-ALI-SINA UNIVERSITY, HAMEDAN, IRAN
 
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.

 
Keyword(s): 4-HYDROXY-3-NITROCOUMARIN, CATECHOL, PAIRED ELECTROCHEMICAL SYNTHESIS, CYCLIC VOLTAMMETRY, 3-AMINO-4- HYDROXYCOUMARIN
 
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