Collect. Czech. Chem. Commun. 1991, 56, 439-448

Synthesis and antibacterial activity of some 1-(2-propynyl) and 1-propadienyl derivatives of 1,4-dihydro-4-oxoquinoline-3-carboxylic acids and similar heterocycles

Stanislav Rádl, Lenka Kovářová and Jiří Holoubek

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


N-Alkylation of IIIa, IIIb, IIId - IIIf and 9-acridanone with 3-bromopropyne in dimethyl sulfoxide in the presence of potassium carbonate yielded N-(2-propynyl) derivatives IVa - IVe and VIa, respectively. Ethyl esters IVa, IVb, and IVe were hydrolyzed to IVf - IVh, respectively. Compounds IVf, IVg, IVctreated with bases yielded N-propadienyl derivatives Va - Vc. On the other hand 2-substituted compounds IVd and IVh did not change under the same conditions. Compound VIa treated with powdered potassium hydroxide in dimethyl sulfoxide at room temperature yielded N-(1-propynyl) derivative VII.