Abstract
Electrochemical oxidation of 4–methylesculetin has been studied in the presence of arylsulfinic acids as nucleophiles in aqueous/ acetonitrile solution mixture, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-quinone derived from oxidation of 4–methylesculetin undergoes a 1,6–Michael addition reaction with unique selectivity, converts to the corresponding new sulfone derivative of esculetin. The reaction products were derived with good yields and excellent selectivity based on electrochemical oxidation under controlled potential conditions at a carbon electrode in an undivided cell.
Keywords: 4-Methylesculetin, 1, 6-Michael addition, arylsulfinic acids, cyclic voltammetry, electrochemical synthesis.
Current Organic Chemistry
Title:Electro-Organic Synthesis of New Esculetin Derivatives Based on 1,6-Conjugate Addition
Volume: 17 Issue: 8
Author(s): Hamid Salehzadeh, Mohammad Rafiee, Davood Nematollahi and Hadi Beiginejad
Affiliation:
Keywords: 4-Methylesculetin, 1, 6-Michael addition, arylsulfinic acids, cyclic voltammetry, electrochemical synthesis.
Abstract: Electrochemical oxidation of 4–methylesculetin has been studied in the presence of arylsulfinic acids as nucleophiles in aqueous/ acetonitrile solution mixture, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-quinone derived from oxidation of 4–methylesculetin undergoes a 1,6–Michael addition reaction with unique selectivity, converts to the corresponding new sulfone derivative of esculetin. The reaction products were derived with good yields and excellent selectivity based on electrochemical oxidation under controlled potential conditions at a carbon electrode in an undivided cell.
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Cite this article as:
Salehzadeh Hamid, Rafiee Mohammad, Nematollahi Davood and Beiginejad Hadi, Electro-Organic Synthesis of New Esculetin Derivatives Based on 1,6-Conjugate Addition, Current Organic Chemistry 2013; 17 (8) . https://dx.doi.org/10.2174/1385272811317080010
DOI https://dx.doi.org/10.2174/1385272811317080010 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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