title: Electrochemical synthesis based on the oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nucleophiles.
abstract: Electrochemical syntheses of new arylthiobenzazoles were carried out by electrochemical oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole. Our voltammetric data indicate that electrochemically generated p-quinone imine participates in a Michael addition reaction with 2-SH-benzazoles leading to the disubstituted 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone. Also, a plausible mechanism for the oxidation of 1-(4-(3,5-bis(benzo[d]thiazol-2-ylthio)-4-hydroxyphenyl) in the presence of p-toluenesulfinic acid is presented. 1-(4-(3,5-Bis(benzo[d]thiazol-2-ylthio)-4-hydroxyphenyl) was converted into 2-(benzo[d]thiazol-2-ylthio)-6-tosylcyclohexa-2,5-diene-1,4-dione through a Michael-type addition of p-toluenesulfinic acid to anodically generated p-quinone imine, replacing 2-mercaptobenzothiazole and followed by hydrolysis.
authors.affiliation: Faculty of Chemistry, Bu-Ali-Sina University, Hamedan 65178-38683 I. R., Iran.
authors.forename: Amene
authors.initials: A
authors.lastname: Amani
authors.forename: Davood
authors.initials: D
authors.lastname: Nematollahi
mesh_terms: D060326:Chemistry Techniques, Synthetic; D004563:Electrochemistry; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C581531:1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone; D010879:Piperazines