SYNTHESIS OF N-SUBSTITUTED (Z)-3-ARYLBENZO[c]THIOPHEN-1(3H)-IMINES BY THE REACTION OF 1-[ARYL(METHOXY)METHYL]-2-LITHIOBENZENES WITH ISOTHIOCYANATES FOLLOWED BY ACID-MEDIATED CYCLIZATION

摘要

A simple procedure for the preparation of N-substituted (Z)-3-arylbenzo[c]thiophen-1(3H)-imines has been developed. Thus, bromine/lithium exchange between 1-[aryl(methoxy)methyl]-2-bromobenzenes and butyllithium, followed by reaction of the resulting 1-[aryl(methoxy)methyl]-2-lithiobenzenes with aliphatic and aromatic isothiocyanates, yields the corresponding N-substituted 2-[aryl(methoxy)methyl]benzothioamides. These were treated with concentrated hydrobromic acid to give the desired products.