Letters in Organic Chemistry

Miguel Yus  
Universidad de Alicante Apdo
Alicante
Spain

Back

Investigation of Electrochemically Induced Michael Addition Reactions of Ortho- and Para-banzoquinones with 2-Mercaptobenzimidazole: Application to Electrosynthesis

Author(s): Davood Nematollahi, Saied S.H. Davarani, Pari Mirahmadpour and Fahimeh Varmaghani

Affiliation: Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, 65178-38683.

Keywords: Catechol, Hydroquinone, Electrochemical synthesis, Thioimidazole, Cyclic voltammetry, Michael addition reaction.

Graphical Abstract:


Abstract:

Electrochemical oxidation of hydroquinone and catechol derivatives (1a-1d) has been studied in the presence of 2-mercaptobenzimidazole (3) as a nucleophile in water/acetonitrile (85/15, v/v) solutions using cyclic voltammetry. Our results indicate that electrogenerated benzoquinone participated in a Michael addition reaction with 2- mercaptobenzimidazole (3) and via an EC mechanism were converted to the corresponding thioimidazole compounds. These products were obtained in good yields using a carbon electrode in an undivided cell.

Reprint ePrint Rights & PermissionsPrintExport

Article Details

VOLUME: 11
ISSUE: 6
Page: [398 - 402]
Pages: 5
DOI: 10.2174/1570178611666140207220757