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

Table 1

The synthesized compound and the synthetic procedure followed.

No.	Synthesized compound	Synthetic procedure
1	Acetanilide	An acetanilide was prepared by refluxing a mixture of aniline (25 mL) and acetic anhydride (25 mL) in a 250 mL round-bottom flask containing zinc powder (0.4 g) for an hour, and 200 mL crushed ice water was used to precipitate the yield. The yield was 23 g (62.3%); mp 112-113°C
2	2-Chloroquinoline-3-carbaldehyde (4)	Vilsmeier reagent was prepared by putting 29 mL (0.375 mol) of N,N-dimethylformamide in a 200 mL round-bottom flask, with a drying tube fitted to its neck, and it was cooled to 5°C using an ice bath. Then phosphorus oxychloride (98 mL, 1.05 mol)) was added to it dropwise from a dropping funnel while being stirred with a magnetic stirrer over a period of 30 min. Then, acetanilide (20.55 g, 0.15 mol) was added to the aforementioned mixture. After 5 minutes, the dropping funnel was replaced by an air condenser with a drying tube at its end, and it was heated at 90–95°C for 22 hours. The mixture was cooled to room temperature and poured into 400 mL crushed ice while being stirred mechanically. The precipitate was collected by suction filtration. The crude product was 17.5 g (61%)
3	(Z)-2-chloro-3-styrylquinoline (5)	A solution prepared by dissolving 0.4 g pellets of KOH in 1 mL water was added dropwise to a mixture of 2-chloroquinoline-3-carbaldehyde (0.5 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. The stirring was continued for 5 hrs at which TLC analysis showed the complete consumption of 2-chloroquinoline-3-carbaldehyde. Then, the mixture was poured to 100 mL crushed ice water, and the precipitate was collected with suction filtration. The crude product was 0.62 g, 89.8%