Synthesis of Reactive s-Triazines Bearing a Cage System Derived from Adamantane as Precursors of Hexamethylmelamine Analogues

The synthesis of reactive s-triazines from cyanuric chloride and 1adamantanamine, I-adamantanol, 2-adamantanol, I-adamantanemethanol and their use in the preparation of structural analogues of hexamethylmelamine are described.Cyanuric chloride (1) is a well known and very important compound which has been used in s-triazines synthesis.'Because of the polyfonctionality of cyanuric chloride, access to s-triazines by nucleophilic substitution with C-C, C-N orland C-0 bond formation has extendly been ac~omplished.~Some s-triazine derivatives have been studied for their interesting biological properties, for example hexamethylmelamine (HMM) (Scheme 1) and 2-amino-4-morpholino-s-triazine ' are clinically used respectively for their antitumoral and antiviral activities.Other works report numerous investigations on molecules in which various biological activities are enhanced by the presence of an adamantyl blocS~"