Dimethyl Sulfide → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

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 RT overnight. The solvent was removed in vacuo, and the residue was triturated and stirred with Et2O (150 mL). The solid was collected, washed with additional Et2O, and dried to afford the title compound (3.4 g, 77%): MS (ES) m/e 179.0 (M+H)+.

Provenance & Evidence