A Facile Route to Melaminophenyl Boronates using 2, 4-Diazido-6- Chloro-1, 3, 5-Triazine as an Electrophilic Reagent

We have synthesised a novel class of melaminyl derivative, containing a phenyl boronate or boronate ester group. The synthetic methodology employed was designed to be facile involving the use of 2, 4-diazido-6-chloro-1, 3, 5-triazine as an electrophilic reagent for nucleophilic substitution of chlorine with a weakly reactive amine. The reagent was chosen with a view to improve the organic solubility of the product and aid isolation by allowing the reaction to be followed by fluorescence quenching (Tlc, F234) and IR (the presence of two N3 peaks).