With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1593-08-4,2-Formylquinoxaline,as a common compound, the synthetic route is as follows.
Quinoxaline-2-carbaldehyde 626 (1.58 g, 10 mmol) was dissolved in EtOH (150 mL) and 1, 4-xylylenediamine (0.63 g, 4.6 mmol) was then added and mixture was stirred at 75 C for 3 h. The mixture was then cooled to room temp and the precipitate was filtered and washed with EtOH (¡Á3) to give the intermediate diimine as an off-white solid (1.82 g, 95%); mp = 185-186 C. The diimine (1.81 g, 4.3 mmol) was dissolved in MeOH (50 mL) and then cooled over an ice bath. Sodium cyanoborohydride (273 mg, 4.3 mmol) and acetic acid (4 mL) were added to the cooled solution and the suspended solid dissolved gradually whilst the mixture was stirred at room temp for 3 h. The volatile components were evaporated under diminished pressure. Ethyl acetate was then added to residue and this was then washed with aq NaHCO3. The aq layer was further extracted with EtOAc (3 ¡Á 10 mL). The combined organic layer was dried (MgSO4), filtered and the solvent was removed. Chromatography of the residue (EtOAc-MeOH, 2:1) gave 7 as a dark red solid (1.31 g, 72%); mp = 116-117 C; 1H NMR (CDCl3, 500 MHz): delta = 8.88 (s, 2H), 8.05-8.09 (m, 4H), 7.70-7.76 (m, 4H), 7.35 (s, 4H), 4.16 (s, 4H), 3.92 (s, 4H), 2.23 (s, 2H, NH); 13C NMR (125 MHz, CDCl3) delta 154.9 (C), 145.3, 141.9, 141.8 (each CH), 138.7 (C), 130.0, 129.3, 129.2, 129.0, 128.4 (each CH), 53.4, 52.8 (each CH2). HRMS (ESI): Found 443.1960 [M+Na]+, C26H24N6Na requires 443.1968.
1593-08-4, 1593-08-4 2-Formylquinoxaline 594088, aquinoxaline compound, is more and more widely used in various fields.
Reference£º
Article; Jarikote, Dilip V.; Li, Wei; Jiang, Tao; Eriksson, Leif A.; Murphy, Paul V.; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 826 – 835;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider