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.
Synthesis of 5-Dialkylaminothiocarbonylthiobarbituric Acids and 5-Diethylaminothiocarbonylthio-6-aminouracil.-Three different procedures are utilized to synthesize the title compounds (III), (V) and (IX). The first one uses the electrophilic property of thiuram disulfides (I). The second one, cf. (VI) → (V), seems to be a nucleophilic substitution at the tetragonal carbon in 2-position. The third procedure using Ph-I(OAc) 2 , cf. (VIII) → (IX), first converts the dicarbonyl system into a betaine containing a weakly nucleophilic anionic part and an electrophilic iodonium part. -(NEILANDS, O. YA.; SUDMALE, I.; SCHNELL, B.; GEORGIEVA, K.; KAPPE, T.; J.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.