SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW QUINOLINE AND 1H-PYRAZOLO[3,4-b]QUINOLINE DERIVATIVES

Document Type : Original Article

Authors

1 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt

2 Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, Egypt

Abstract

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.