Synthesis of 5‐dialkylaminothiocarbonylthiobarbituric acids and 5‐diethyiaminothiocarbonylthio‐6‐aminouracil

Abstract

The title compounds are obtained by three different methods. The aminothiocarbonylthiolation of barbituric acids 1 and aminouracil (5) can be accomplished in one step by reaction with thiuram disulfides in the presence of potassium carbonate. On the other hand, compounds 4 can be obtained via the salt of chloro derivative 2 or the corresponding iodonium ylides 3. The aminouracil derivative 7 was obtained in a similar fashion from 5 directly or via iodonium betaine 6.

A Simple, Convenient One‐Pot Synthesis of Dithio‐Carbamide Derivatives of Heterocyclic 1,3‐Dicarbonyl Systems

“…The sulfinylation of heterocyclic 1,3‐dicarbonyl systems, such as 4‐hydroxy‐2‐quinolones and 4‐hydroxy‐coumarins and 4‐hydroxy‐2‐pyrones, 6‐hydroxy‐4‐pyrimidones, 4‐hydroxy‐2‐pyridones, 4‐hydroxy‐6‐pyridazones, and 5‐hydroxy‐3‐pyrazolones , was reported earlier. The introduction of the dialkylaminothiocarbonylthio group directly at the 5‐position of barbituric acid with tetraalkylthiuram disulfides is more effective than reactions via the 5‐chloro derivative or 5‐phenyliodonium yields . The equimolar amount of the aliphatic tetraalkylthiuram disulfides is used for the sulfinylation.…”

“…The equimolar amount of the aliphatic tetraalkylthiuram disulfides is used for the sulfinylation. Aromatic thioethers are prepared by the reaction of 3‐chloro‐4‐hydroxy‐2‐pyridones or their 3‐phenyl‐iodonium yields . Oxidation of the aliphatic thioethers is not possible like the aromatic thioethers under similar reaction conditions.…”