Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones.
Gérard Klein, Achyuta N Acharya, John M Ostresh, Richard A Houghten
Index: J. Comb. Chem. 4(4) , 345-51, (2002)
Full Text: HTML
Abstract
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.
Related Compounds
Related Articles:
1997-01-01
[Mol. Divers. 3(2) , 117-20, (1997)]
Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation.
2004-05-01
[Comb. Chem. High Throughput Screen 7(3) , 251-5, (2004)]
Reagents for the preparation of chromophorically labeled polyethylene glycol-protein conjugates.
1993-05-01
[Anal. Biochem. 210(2) , 258-61, (1993)]
Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters.
2015-03-26
[Eur. J. Med. Chem. , doi:10.1016/j.ejmech.2013.06.025, (2013)]
2011-06-06
[Chem. Asian J. 6(6) , 1557-65, (2011)]