Electrochemical synthesis based on the oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nucleophiles.

Article Details

Citation
Copy to clipboard

Amani A, Nematollahi D

Electrochemical synthesis based on the oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nucleophiles.

J Org Chem. 2012 Dec 21;77(24):11302-6. doi: 10.1021/jo302418p. Epub 2012 Dec 13.

PubMed ID
23198901 [ View in PubMed
]
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.

DrugBank Data that Cites this Article

Drugs