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Perhaloketones XIX . Derivatives of benzo‐ N ‐heterocycles
Author(s) -
Gilbert Everett E.
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060406
Subject(s) - chemistry , moiety , hydrate , anhydrous , indole test , ring (chemistry) , imidazole , medicinal chemistry , aminal , organic chemistry , cleavage (geology) , stereochemistry , geotechnical engineering , fracture (geology) , engineering
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.