oa South African Journal of Chemistry - 1-alkyl-1, 4-dihydro-4-iminoquinoline-3-carboxylic acids : synthesis, structure and properties
|Article Title||1-alkyl-1, 4-dihydro-4-iminoquinoline-3-carboxylic acids : synthesis, structure and properties|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Author||T. Van Es and B. Staskun|
|Publication Date||Jan 2002|
|Pages||13 - 33|
|Keyword(s)||Charge transfer structure, Intramolecular hydrogen bonds, Mechanism, Quinolin-4-imines and Research articles|
1-Alkyl-1, 4-dihydro-4-iminoquinoline-3-carboxylates undergo neutral hydrolysis (in H2O or H2O-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-H2O 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.
Article metrics loading...