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

Abstract

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).