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, 1H NMR, 13C NMR, and mass). Furthermore, some of these synthesized compounds were screened for their biological activities against various pathogenic bacterial and fungal strains. Our results demonstrate that most of the synthesized compounds possess a significant broad antibacterial activity against all strains of both gram-positive and gram-negative bacteria. In addition, compound 5 showed remarkable antifungal activity. 8-Bromo-3-cyano-6- fluoroquinoline-4(1H)-one (4) was taken as a versatile building block to synthesize the thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. The biological activities of some synthesized compounds were assessed through their action on fungi and bacteria. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.