Water → 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile
Reaction equation
Br[C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.O.[CH3:13][N:14]1CCCC1=O>>[NH:9]1[CH2:8][CH2:7][O:6][C:5]2[N:10]=[CH:11][C:2]([C:13]#[N:14])=[CH:3][C:4]1=2Participants
4
Procedure
In a 5 ml flask, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (24 mg, 0.111 mmol) was dissolved in N-methylpyrrolidone (NMP) (20.3 ml), and cuprous cyanide (CuCN) (16 mg, 0.178 mmol) was added thereto and then stirred in microwave at 180□ for 10 minutes using microwave (100 W) apparatus. The reaction mixture was cooled to room temperature and water (10 ml) was added thereto, and extracted with ethyl acetate (10 ml*2). The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=20:1. The fractions containing the product were collected and evaporated to obtain pale-yellow solid (17 mg, quantitative yield).