Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones
Article
Klein, G, Acharya, AN, Ostresh, JM et al. (2002). Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones
. 4(4), 345-351. 10.1021/cc010089k
Klein, G, Acharya, AN, Ostresh, JM et al. (2002). Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones
. 4(4), 345-351. 10.1021/cc010089k
An efficient method for the solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4-(3H,10H)-diones from resin-bound amino acids is described. N-acylation of the primary amine of a resin-bound amino acid with 4-fluoro-3-nitrobenzoic acid, followed by displacement of the fluoro group and reduction of the nitro group, generated a resin-bound o-dianilino derivative. The dianilino compound was treated with cyanogen bromide to generate the corresponding iminobenzimidazole, which, following treatment with N-(chlorocarbonyl)isocyanate, afforded the resin-bound triazinodione derivative. Alkylation of the triazinodione compound with an alkyl halide yielded, following cleavage of the solid-support, the trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-dione.
