4-(2-Hydroxyaryl)-1,2,3-selenadiazoles as Precursors of Benzofuran-2-selenolates

The reaction of selenium dioxide with o-hydroxyacetophenone semicarbazones gives 4-(2-hydroxyaryl)-1,2,3-selenadiazoles which undergo ready decomposition by the action of potassium carbonate to form benzofuran-2-selenolates. The latter can be alkylated with methyl iodide and benzyl chloride and arylated with 2,4-dinitrochlorobenzene. Intermediate formation of 2-(o-hydroxyphenyl)ethyneselenolate during decomposition of 1,2,3-selenadiazoles was proved by the isolation of methyl o-methoxyphenylethynyl selenide when the substrate was treated with potassium carbonate in the presence of methyl iodide.