4-Hydroxy-6-methylchromen-2-thione, and a sulphur analogue of dicoumarol

Abstract

The interaction of 2-hydroxy-5-methylacetophenone, carbon disulphide, and sodium 1,1-dimethylpropyl oxide gives 4-hydroxy-6-methylchromen-2-thione (I) along with another compound believed to be a trithiolan derivative (IV). The general properties and structure of the hydroxychromenthione are discussed and various reactions described, notably methylation to 6-methyl-2-methylthiochromen-4-one (Xb), oxidation to the disulphide (XII), and condensation with formaldehyde to give a sulphur analogue (XV) of dicoumarol.