反应详情

温度

-78 °C

6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one (6.2 g, 27 mmole) was dissolved in 5:1 CH2Cl2/MeOH (500 mL) and the solution was cooled to −78° C. Ozone was bubbled through the solution with stirring until a pale blue color appeared, then the excess ozone was removed by bubbling oxygen through the solution for 15 min. Dimethylsulfide (9.9 mL, 135 mmole) was added to the solution, and the reaction was stirred at −78° C. for 3 hr, then at room temperature overnight. The solvent was removed in vacuo, and the residue was triturated and stirred with Et2O (150 mL). The solid was collected by suction filtration, washed with additional Et2O, and dried to afford the title compound (3.4 g, 77%): LC-MS (ES) m/e 179 (M+H)+.

1. customOzone was bubbled through the solution
2. customthe excess ozone was removed
3. customby bubbling oxygen through the solution for 15 min
4. stirringthe reaction was stirred at −78° C. for 3 hr
5. customat room temperature
6. customovernight
7. customThe solvent was removed in vacuo
8. customthe residue was triturated
9. stirringstirred with Et2O (150 mL)
10. filtrationThe solid was collected by suction filtration
11. washwashed with additional Et2O
12. customdried