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Klein G, Acharya AN, Ostresh JM, et al. Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones. J Comb Chem. 2002;4(4):345-51doi: 10.1021/cc010089k.
Klein, G., Acharya, A. N., Ostresh, J. M., & Houghten, R. A. (2002). Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones. Journal of combinatorial chemistry, 4(4), 345-51. https://doi.org/10.1021/cc010089k
Klein, Gérard, et al. "Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones." Journal of combinatorial chemistry vol. 4,4 (2002): 345-51. doi: https://doi.org/10.1021/cc010089k
Klein G, Acharya AN, Ostresh JM, Houghten RA. Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones. J Comb Chem. 2002 Jul-Aug;4(4):345-51. doi: 10.1021/cc010089k. PMID: 12099852.
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J Comb Chem. 2002 Jul-Aug;4(4):345-51. doi: 10.1021/cc010089k.

Parallel solid-phase synthesis of trisubstituted triazinobenzimidazolediones.

Journal of combinatorial chemistry

Gérard Klein, Achyuta N Acharya, John M Ostresh, Richard A Houghten

Affiliations

  1. Torrey Pines Institute for Molecular Studies, 3550 General Atomics Court, San Diego, California 92121, USA.

PMID: 12099852 DOI: 10.1021/cc010089k

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.

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