Electric Literature of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.
In a 100 mL flask, 2,3-pyrazinedicarboxylic anhydride 12 (0.7505 g, 5 mmol) was reacted with 2 (1.0511 g, 5 mmol) in dry THF (10 mL) stirred overnight at rt. The mixture was transferred to a separatory funnel and extracted with CH 2 Cl 2 (3 x 10 mL) and NaOH (1N) (10 mL). The organic phase was separated and HCl (1N) (10 mL) was added to the aqueous phase until a pH=2 was reached and a precipitate formed. The solid was filtered and washed with water (20 mL), and concentrated under reduced pressure to provide 13 (1.73 g, 4.8 mmol, 96%), as a yellow solid. 1 H NMR (400 MHz, DMSO-d 6 ) delta 1.33 (3H, t, J = 7.02 Hz), 2.51 (4H, d, J = 1.59 Hz), 4.46 (2H, q, J = 7.01 Hz), 7.21 (1H, t, J = 7.52 Hz), 7.47 (1H, t, J = 7.66), 7.59 (1H, d, J = 4.10 Hz), 7.61 (1H, d, J = 3.48 Hz), 7.73 (1H, d, J = 7.27 Hz), 8.58 (1H, s), 8.63 (2H, s); 13 C NMR (100 MHz, DMSO-d 6 ) delta 14.2, 37.5, 109.4, 109.7, 110.95, 119.1, 119.7, 120.6, 122.3, 122.6, 126.2, 131.8, 136.8, 140.5, 141.8, 144.8, 145.8, 164.3. LC/MS (ESI) m/z 361.1292 [M+H + ].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Pyrazinecarboxylic anhydride, its application will become more common.
Reference:
Article; Vlaar, Cornelis P.; Castillo-Pichardo, Linette; Medina, Julia I.; Marrero-Serra, Cathyria M.; Velez, Ericka; Ramos, Zulma; Hernandez, Eliud; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 884 – 890;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem