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Perhaloketones XIX . Derivatives of benzo-N-heterocycles
Authors:Everett E Gilbert
Abstract:A study was made of the behavior of imidazole and six benzo-N-heterocyclic compounds upon direct treatment with anhydrous and hydrated hexafluoro- and sym-tetrafluorodichloroacetones. Two of the compounds did not react, and four gave addition compounds. Indole reacted with both ketones in the 3-position. Heterocyclic precursors were made by reacting o-phenylenediamine, o-aminophenol, and o-aminobenzenethiol with hexafluoroacetone hydrate, thus introducing the 2-hydroxyhexafluoro-2-propyl moiety into the ring para to the amino group. A similar product was made from o-phenylenediamine and tetrafluorodichloroacetone. These compounds were then converted to twenty-eight heterocyclic derivatives. Four of the latter underwent haloform cleavage of the hydroxyhexahalopropyl group, a novel, but not widely applicable, preparative approach to the corresponding heterocyclic carboxylic acids.
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