Electric Literature of 18368-73-5 ,Some common heterocyclic compound, 18368-73-5, molecular formula is C6H6N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of 250 mg (1.86 mmol) of terephthalaldehyde 70, 618 mg (4.47 mmol) of nitropicoline 63 in 8 mL of THF was added 4.47 mL (4.47 mmol) of a 1 M solution of TBAF and 732 mg (5.59 mmol) of Huenig’s base. The mixture was stirred at 60 C for 3 days. The crude reaction mixture was concentrated under reduced pressure onto 1 g of silica gel and purified by silica gel chromatography with a gradient of 0e55% EtOH/EtOAc:hexane to afford 400 mg (68%) of dimeric furopyridine 73 as a colorless solid: mp 157e158 C; 1 H NMR (500 MHz, CDCl3) d 3.23 (dd, 2H, J 16.1 and 7.6 Hz), 3.71 (dd, 2H, J 16.1 and 9.4 Hz), 5.86 (dt, 2H, J 9.4 and 7.6 Hz), 6.85 (m, 2H), 7.45 (s, 4H), 7.50 (m, 2H), 8.01 (d, 2H, J 5.0 Hz); 13C NMR (125 MHz, CDCl3) d 36.4, 36.5, 8.10, 116.7, 119.0, 125.6, 133.4, 141.0, 146.6, 167.7. Anal. Calcd. For C20H16N2O2: C, 75.93; H, 5.10; N, 8.86. Found: C, 75.76; H, 4.98; H, 8.79.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18368-73-5, its application will become more common.
Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem