Synthesis and antimicrobial activity of some new quinoline and 1h-pyrazolo[3,4-b]quinoline derivatives

Vilsmeier formylation of acetanilide I followed by treatment with hydroxylamine produced 2-chloroquinoline-3-carbonitrile II that was condensed with different amines to give 2- substituted aminoquinolines-3-carbonitriles III. Treatment of II with thiourea yielded 2- mercaptoquinoline-3-carbonitrile IV, which was converted to its potassium salt V that was condensed with some chloroacetate esters to produce 2-substituted thioquinoline-3- carbonitriles VI. Hydrazinolysis of II or IV gave 1H-pyrazolo[3,4-b]quinolin-3-ylamine VII. Condensation of VII with different aryl aldehydes resulted in the corresponding imines VIII. Treatment of VII with p-chloro-benzoyl chloride afforded the amide IX. Some of the synthesized compounds were evaluated for their antibacterial and antifungal activity