42484-83-3Relevant articles and documents
Convenient Synthesis of 2,7-Disubstituted 5H-1,3,4-Thiadiazolopyrimidin-5-ones and Related Compounds
Tsuji, Tadakazu,Takenaka, Keiko
, p. 637 - 638 (1982)
2,7-Disubstituted 5H-1,3,4-thiadiazolopyrimidin-5-ones were synthesized from the reaction of 3-amino-6-methyl-2-thiouracil with carboxylic acid or from that of thiosemicarbazide with carboxylic acid and β-keto ester in the presence of phosphorus pentaoxide and methanesulfonic acid.The synthesis of related compounds is also described.
Reaction of β-Keto Esters with 2-Amino-1,3,4-thiadiazoles. A Reinvestigation
Kornis, Gabriel,Marks, Pamela J.,Chidester, Constance G.
, p. 4860 - 4863 (2007/10/02)
2-Amino-5-substituted-1,3,4-thiadiazoles react with ethyl acetoacetate under basic conditions to give 3-oxo-N-(5-substituted-1,3,4-thiadiazol-2-yl)butanamides 4.During acid cyclization, 4 rearranges to give a mixture of thiadiazolopyrimidones 3 and 5, the ratio varying with the nature of the substituents.Under acidic conditions, the butenoic ester 2 can also be isolated; however, it does not rearrange and yields only the expected 3.With ethyl benzoylacetate under acidic and basic conditions, only one compound is formed whose structure was determined as the enol form of 4d by X-ray diffraction.In strong acid, it also cyclizes and rearranges to give a mixture of 3 and 5 in a 9:1 ratio.