Synthesis, reactions, and biological activities of some new thieno[3,2-c]quinoline and pyrrolo[3,2-c]quinoline derivatives.

2-Bromo-4-fluoroaniline (1) was condensed with ethyl 2-cyano-3-ethoxyacrylate (2) in ethanol to afford 3, which upon refluxing in paraffin oil at 250°C gave 8-bromo-3-cyano-6-fluoroquinoline-4(1H)-one (4). Then, compound 4 was taken as a versatile building block that allows the synthesis of thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. The newly synthesized compounds and their derivatives were characterized by elemental analysis and spectroscopy (IR, (1)H NMR, (13)C NMR, and mass).