Collect. Czech. Chem. Commun. 1984, 49, 1722-1730

Thioxanthene derivatives with neurotropic activity; synthesis of 9-(3-dimethylaminopropylidene)-2-(methylthiomethyl)thioxanthene and of some related compounds

Vojtěch Kmoníček, Václav Bártl and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


A reaction of 2-(bromomethyl)thioxanthone with sodium methanethiolate with sodium methanethiolate gave 2-(methylthiomethyl)thioxanthone (II) which was transformed by treatment with 3-dimethylaminopropylmagnesium chloride to the tertiary alcohol IV. Its dehydration by heating with dilute sulfuric acid afforded the title compound I. An attempt at preparing the analogous 2-(methoxymethyl) derivative proceeded similarly but failed in the stage of the acid-catalyzed dehydration of the tertiary alcohol V. Acids VIII-XII and the nitrile XIII were prepared as potential intermediates. Compound I has properties of a tranquilizer with a weak cataleptic activity.