Synthesis and reactivity of benzoxa(thia)zol-2-thiones: new route to 2-alkylthiobenzoxa(thia)zoles

摘要

The reaction of aromatic primary amines 1 with carbon disulfide in the presence of a catalytic amount of triethylamine followed by treatment with aqueous hydrogen peroxide leads to the corresponding benzoxa(thia)zol-2-thiones 3a-c which can be transformed with iminoethers into 2-alkylthiobenzoxa(thia)zoles 5a-b in good yields (64-85%).