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.
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