4747-75-5Relevant articles and documents
Manipulation of N,O-nucleophilicity: Efficient formation of 4-N-substituted 2,4-dihydro-3H-1,2,4-triazolin-3-ones
Huang, Xianhai,Palani, Anandan,Xiao, Dong,Aslanian, Robert,Shih, Neng-Yang
, p. 4795 - 4798 (2004)
(Chemical Equation Presented) A new efficient two-step synthesis of 2,4-dihydro-3H-1,2,4-triazolin-3-ones (triazolinones) from readily available amines is reported. Our novel conditions using hexamethyl disilazane, bromotrimethylsilane, and a catalytic amount of ammonium sulfate smoothly cyclize 1-formyl and 1-acetyl semicarbazides to the target triazolinones. This transformation features simultaneous manipulation of N- and O-nucleophilicity as well as differentiation of the nucleophilicity of a urea and an acyl carbonyl.