Syntheses of N-Substituted Thymine Thioacetamides. A Novel Approach to Site Selective Acylation of Diaminoalkanes

A new series of N-substituted thiocarbamoyl derivatives containing histamine, tryptamine, and other moieties having at least one amino group attached to an aliphatic chain, has been synthesized from (1-thyminyl)thioacetamide in good isolated yields (69–86%). N-[2-(4-Imidazolyl)ethyl](1-thyminyl)thioacetamide was hydrolyzed to its amide on prolonged heating in water. Ammonium sulfide (20–22% solution in water) has found interesting new applications in the efficient synthesis of N-[2-(3-indolyl)ethyl](1-thyminyl)thioacetamide and site selective acylation of diaminoalkanes, starting directly from nitriles.