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Solid-phase synthesis of substituted benzimidazoles

Tumelty, David ; Schwarz, Matthias K. ; Cao, Kathy ; Needels, Michael C.

Tetrahedron letters, 1999-08, Vol.40 (34), p.6185-6188 [Periódico revisado por pares]

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Título:
Solid-phase synthesis of substituted benzimidazoles
Autor: Tumelty, David ; Schwarz, Matthias K. ; Cao, Kathy ; Needels, Michael C.
É parte de: Tetrahedron letters, 1999-08, Vol.40 (34), p.6185-6188
Descrição: A solid-phase synthesis of benzimidazoles, substituted on the aromatic ring by a variety of groups or atoms, is described. Intermediate 3, derived from the acylation of a resin-bound secondary amine with Fmoc-glycine, was eleborated via nucleophilic displacement with substituted o-halo-nitroarenes to give 4. Careful optimization of the subsequent nitro-group reduction and cyclization with aldehydes, followed by acidolysis gave the title compounds 7 in good yields and purities. From elaboration of a resin-bound amine 2, intermediates 4 were synthesized via nucleophilic displacement with a variety of substituted o-haloarenes. Subsequent nitro-group reduction, cyclization with aldehydes under carefully optimized conditions and acidolysis furnished a diverse assortment of ring-substituted benzimidazoles 7 in good yields and purities.
Editor: Elsevier Ltd
Idioma: Inglês

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