Reaction of 3-oxodihydrothionaphthenes with aryl diazonium chlorides and aryl isothiocyanates

Abstract

The reaction of 3-oxodihydrothionaphthenes with aryl diazonium chlorides gives 2-arylhydrazono-3-oxodihydrothionaphthenes. By oxidation of the latter with hydrogen peroxide in glacial acetic add, new 2-arylhydrazonodihydrothionaphthene-(3)-one-1, 1-dioxides are synthesized. Condensation of aryl isothiocyanates with 3-oxodihydrothionaphthenes in tetrahydrofuran gives 2-(arylthiocarbamyl)-3-oxodihydrothionaphthenes; cyclization of the latter with ω-bromoacetophene leads to the synthesis of 4-phenyl-3-aryl-2-(3′ -oxodihydrothionaphthylidene-2′)-Δ⁴-thiazolines.