An Efficient and Eco-Friendly Procedure for Electrophilic Thiocyanation of Anilines and 1-(Substituted benzylidene)-2-phenyl Hydrazines

Abstract

Thiocyanates form an important class of organic compounds commonly found in natural products that exhibit excellent antimicrobial activity. The electrophilic thiocyanation is one of the most effective methods of introducing a -SCN functional group to the parent organic molecule. In this work, we explored an eco-friendly and highly efficient method for thiocyanation of anilines and 1-(substituted benzylidene)-2-phenylhydrazines using commercially available N-bromoscuccinimide (NBS) and potassium thiocyanate (KSCN). The optimized protocol afforded thiocyanates with good regioselectivity and excellent yields in comparison to the available methods.

Keywords

• N-bromosuccinimide
• KSCN
• aromatic amines
• schiff bases
• electrophilic thiocyanation