1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 2.1 Hydrolysis and rearrangement products

Theodorus Van Es*, Benjamin Staskun

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The title compounds, while relatively stable in acid solution, undergo basic hydrolysis to afford the corresponding 1-alkyl-4-oxo-3-quinolinecarboxylic acids. Preferential removal of the 4-imino function may be achieved in dilute alkali. Neutral (H2O) hydrolysis yields a 4-oxo-3-quinolinecarboxylic ester together with an unusual water-soluble, dipolar 4-imino-3- quinolinecarboxylic acid. Some properties and reactions of the latter are described. Certain of the title imino esters, specifically those bearing electron-withdrawing substituents in the carbocyclic framework, undergo a novel rearrangement in basic medium to afford 2(1H)-quinolone derivatives; in other instances the outcome is a 2-acetimidoyl-N-alkylaniline derivative. A tentative pathway for the D2O-exchange, undergone at room temperature by the 2-methyl protons of the title imino esters and related compounds, is presented.

Original languageEnglish
Pages (from-to)121-126
Number of pages6
JournalSouth African Journal of Chemistry
Volume51
Issue number3
Publication statusPublished - 1998

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