Traceless solid-phase synthesis of 6-amino- and 6-hydroxyimino-1,3,5-triazine-2,4-diones and 1,3,5-triazine-2,4,6-triones.

A traceless solid-phase synthesis of 6-amino- and 6-hydroxyimino-1,3,5-triazine-2,4-diones and 1,3,5-triazine-2,4,6-triones has been developed. The strategy comprises of linking a preformed N-carbamothioylcarbamate to bromomethyl resin to give a S-linked isothiourea, which then undergoes cyclization with isocynates to yield the resin-bound 1,3,5-triazine-2,4-diones. Subsequent cleavage was accomplished by either direct substitution with a suitable amine or by oxidative activation of the thioether functionality followed by nucleophilic substitution. Using this synthetic strategy, we prepared a representative set of 31 6-amino-1,3,5-triazine-2,4-diones, 10 6-hydroxyimino-1,3,5-triazine-2,4-diones, and 8 1,3,5-triazine-2,4,6-triones.