[O:1]1[C:10]2[C:5](=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1.[CH2:12]([N:14](CC)CC)C.O>C(#N)C>[O:1]1[C:10]2[C:5](=[N:6][C:7]([C:12]#[N:14])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1Under an argon atmosphere, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 5-oxide (102 mg, 666 μmol) was dissolved in actonitrile (700 μL), added triethylamine (202 mg, 2.00 mmol) and trimethylsilylnitrile (529 mg, 5.33 mmol) at room temperature, and the mixture was stirred at 100° C. overnight. Under ice-cold conditions, water was added, and the reaction solution was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (chloroform/methanol), and the title compound (105 mg (yield 97%)) was obtained as a brown solid.
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