Abstract
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.
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