Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Table 2

Continued table of the synthesized compounds and their synthetic procedure.

No	Synthesized compound	Synthetic procedure
5	(Z)-3-styrylquinolin-2(1H)-one (7)	Aqueous solution of KOH (1 mL, 40%) was added dropwise to a mixture of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (0.45 g, 2.6 mmol) and benzyltriphenylphosphonium chloride (1.01 g, 2.6 mmol) dissolved in 10 mL DMF in a 100 mL round-bottom flask while being stirred with a magnetic stirrer. After stirring for 4 hrs, 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%)
6	2-Methoxyquinoline-3-carbaldehyde (8)	To the mixture of methanol (15 mL) and DMF (15 mL) in a 250 mL round-bottom flask were added chloroquinoline-3-carbaldehyde (1.0 g, 5.2 mmol) and potassium carbonate (1.5 g, 10.8 mmol). A water condenser was fitted to the flask, and the mixture was refluxed for 6 hours. The completion of the reaction was monitored by TLC, and the the excess methanol was removed by distillation. Then, the residue was added to 100 mL ice-cold water after being cooled to room temperature. The precipitate was collected by suction filtration and washed twice with 20 mL ice-cold water. The yield was a gray powder, 87 g (90%); mp 106–108°C