Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material

Abstract

2-Aminobenzoxazoles and 2-mercaptobenzoxazoles were selectively synthesized by treating o-aminophenols with dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithiocarbamates gave 2-aminobenzoxazoles with good yield (70–92%) in one pot manner, and 2-mercaptobenzoxazoles were synthesized (yield: 55–80%) in the presence of K2CO3 by treating o-aminophenols with tetramethylthiuram disulfide (TMTD). The feature of this method includes good to excellent yield, easy performance and broad substrate scope, which makes the protocol practical and attractive in the preparation of some potential pharmaceutically active compounds.