Manipulation of N,O-Nucleophilicity:  Efficient Formation of 4-N-Substituted 2,4-Dihydro-3H-1,2,4-Triazolin-3-ones

Autor: Huang, X., Palani, A., Xiao, D., Aslanian, R., Shih, N.-Y.
Zdroj: Organic Letters; December 2004, Vol. 6 Issue: 25 p4795-4798, 4p
Abstrakt: 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.
Databáze: Supplemental Index