Synthesis of 2- [3-substituted amino2-hydroxypropylthio] -1-methyl-5-oxo-2-imidazoline derivatives of pharmaceutical interest: a new method for desulfurization of 2-thiohydantions

ABSTRACT

The synthesis of novel 2-[3-morpholino- and 3-piperidino- 2-hydroxypropylthio]- 1-methyl-5-oxo- 4-substituted- 2-imidazolines was described. Reaction of the potassium salts of 2- thiohydantoin Ia-g with epichlorohydrin afforded the corresponding 2-[3-chloro- 2-hydroxypropylthio]- 1-methyl-5-oxo- 4-substituted- 2-hydroxypropylthio]- 1-methyl-5-oxo- 4-substituted- 2-imidazolines IIa-g, which decomposed into the hydantoins or piperidine, on the cold, did not produce any product. On heating the mixtures, compounds IIIa-g and the thiiranylmethylamines IVa-b were obtained. Treatment of Ia-g with 3-chloro-2-hydroxypropylamines Va-b on the cold gave no products, but on heating, the reactants decomposed into IIIa-g and IVa-b. Meanwhile, stirring Ia-h with the glycidylamines Vla-b, on the cold, afforded the target compounds VIIa-o which on heating, in neutral or basic medium, underwent desulfurization into compounds IIIa-h and liberation of compounds IVa-b