68329-79-3Relevant academic research and scientific papers
SMILES REARRANGAMENT-XV. THE S-->N TYPE REARRANGEMENT IN URACIL DERIVATIVES
Maki, Y.,Hiramitsu, T.,Suzuki, M.
, p. 2097 - 2100 (2007/10/02)
The reaction of 1,3-dimethyl-6-(2-acetamidophenylthio)uracil 6 with caustic alkali followed by methylation gave 1,3-dimethyl-6-(2-methylthioanilino)uracil 7 accompanied with 1,3-dimethyl-5-acetyl-6-(2-methylthioanilino)uracil 8.Pyrimidobenzothiazepine 10 was obtained in high yield by the Smiles rearrangament of 6, trapping of the resulting thiolate ion with formalin and subsequent acid-catalysed cyclization.Treatment of 1,3-dimethyl-6-(2-aminophenylthio)uracil 5 with hot acetic acid gave 1,3-bis-1,3-dimethylurea 12.Upon heating 5 or N-acetyl derivative 6 in dimethylsulfoxide, 5-thiaisoalloxazine 3 was obtaiined in moderate yield.Mechanism of the observed reactions were discussed.
