Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines
Table 4
Continued table of the synthesized compounds and their synthetic procedure.
No
Synthesized compound
Synthetic procedure
10
(Z)-2-chloro-8-methyl-3-styrylquinoline (14)
1 mL 40% aqueous KOH was added dropwise to a mixture of 2-Chloro-8-methylquinoline-3-carbaldehyde (0.53 g, 2.6 mmol) and benzyltriphenylphosphonium chloride (1.01 g, 2.6 mmol) dissolved in DMF (10 mL) in 100 mL round bottom flask while being stirred with magnetic stirrer. The stirring was continued for 8 hrs at which TLC analysis showed the disappearance of the reactant. Then, the mixture was poured to 100 mL crushed ice water, and the precipitate was collected with suction filtration. The crude product was 0.64 g (88.2%)
2-Chloro-8- methylquinoline-3-carbaldehyde (1.0 g, 5.3 mmol) was refluxed in a mixture of 6 M HCl (10 mL) and glacial acetic acid (15 mL) for 3 hrs with the progress of reaction followed by TLC. At end, the excess acetic acid was removed by distillation under reduced pressure. The residue was added to 50 mL crushed ice cold water, and the precipitate was collected by suction filtration, washed with cold water, and allowed to dry in a wood cupboard. The product was a yellow powder, and the yield was 0.79 g (80.2%); mp 176–178°C
12
(Z)-8-methyl-3-styrylquinolin-2(1H)-one (16)
Aqueous solution of KOH (1 mL, 40%) was added dropwise to a mixture of 8-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (0.50 g, 2.6 mmol) and benzyltriphenylphosphonium chloride (1.01 g, 2.6 mmol) in DMF (10 mL) in a 100 mL round-bottom flask while being stirred with a magnetic stirrer. The stirring was continued for 7 hrs at which TLC analysis showed the complete consumption of the reactant. Then, the mixture was poured to 100 mL crushed ice water, and the precipitate was collected with suction filtration. The crude product was 0.55 g (85%)
