Solid-phase synthesis of N-hydroxyindoles and benzo[c]isoxazoles by C-arylation of substituted acetonitriles and 1,3-dicarbonyl compounds with polystyrene-bound aryl fluorides

Abstract

The reaction of different carbon nucleophiles with resin-bound 4-fluoro-3-nitrobenzoic acid and the chemistry of the resulting products has been investigated. Treatment of Wang resin bound 4-fluoro-3-nitrobenzoic acid with 1,3-dicarbonyl compounds or acceptor-substituted acetonitriles, followed by reduction of the nitro group and cleavage from the support, led to substituted 1-hydroxy-6-indolecarboxylic acids. Treatment of polystyrene-bound 4-fluoro-3-nitrobenzoic acid amides with arylacetonitriles led to 4-aroyl-3-nitrobenzoic acid derivatives, which upon reduction with tin(II) chloride yielded benzo[c]isoxazoles.