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Paper | Regular issue | Vol 91, No. 3, 2015, pp.526-536
Published online, 3rd February, 2015
DOI: 10.3987/COM-14-13154
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

Kazuhiro Kobayashi,* Yuuho Shigemura, and Kosuke Ezaki

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


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.