Solid-Phase Synthesis of 1,3,5-Triazine-2,4-Diones and -2,4,6-Triones

Significance

The solid-phase synthesis of 1,3,5-triazine-2,4-diones 6, 7 and 8 and -2,4,6- triones 9 is described. Thus, resin-bound 1,3,5-triazine-2,4-dione 4 was prepared from bromomethyl resin 1 with N-carbamothioylcarbamate 2 through S-alkylation and cyclization with isocyanates. The sulfide linkage of resin 4 was oxidized with anhydrous dimethyldioxirane (DMDO) in CH₂Cl₂-­acetone to give resin 5. Nucleophilic substitution of resin 5 with ammonium hydroxide, primary amines, and hydroxylamine afforded the corresponding products 6, 7, and 8, respectively. The MCPBA oxidation of 4 gave products 9.