Collect. Czech. Chem. Commun. 1988, 53, 1068-1077

Preparation and spectral properties of imidazo- and triazoloquinolines with angular ring fusion

Viktor Milataa, Dušan Ilavskýa and Ján Leškob

a Department of Organic Chemistry
b Central Laboratory of Chemical Technique, Slovak Institute of Technology, 812 37 Bratislava


The imidazo- and triazolo[4,5-f]quinolines (Va, Vb) and imidazo- and triazolo[4,5-h]quinolines (Xa, Xb) have been synthetized by the Gould-Jacobs reaction starting from the quinolinecarboxylic acids II and VII prepared by base-catalyzed hydrolysis of the esters I and VI, resp. The decarboxylation of the acids II and VII gives the quinolones III and VIII, resp., which are aromatized to the corresponding chloroquinolines IV and IX. The latter compounds give the azoloquinolines V and X on catalytic reduction. The structure of the condensed heterocyclic compounds with angular ring fusion has been proved by 1H and 13C NMR, IR, UV, and mass spectra.