oa South African Journal of Chemistry - 1-alkyl-1, 4-dihydro-4-iminoquinoline-3-carboxylic acids : synthesis, structure and properties

Volume 55, Issue 1
  • ISSN : 0379-4350



1-Alkyl-1, 4-dihydro-4-iminoquinoline-3-carboxylates undergo neutral hydrolysis (in HO or HO-EtOH mixtures) to yield water-soluble 4-iminoquinoline-3-carboxylic acids and the corresponding 4-oxo esters. Such 4-imino acids are also accessed by treating an appropriate 1-alkyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid successively with thionyl chloride and an amine-HO mixture, or from treatment of a 4-imino ester salt with aqueous amine. In the latter procedures 7-fluoro substituted substrates gave rise to 7-alkylamino derivatives even at room temperature. The title compounds are inferred to have an intramolecularly H-bonded charge transfer structure, and some of their chemical reactions and spectral (HRMS, 1H NMR) properties are described.

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