反应详情

温度

20 °C

H2O2 (70%, 0.47 mL, ca. 9.7 mmol) was added dropwise to a stirred solution of TFM (1.35 mL, 9.7 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 20° C. for 10 min, then cooled to 0° C. and added to a solution of 1-oxide 115 (250 mg, 0.97 mmol) and TFA (0.16 mL, 2.07 mmol) in CHCl3 (15 mL) at 0° C. The solution was stirred at 20° C. for 5 h. The solution was made basic with dilute aqueous NH3 solution and extracted with CHCl3 (3×30 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1,4-dioxide 116 (55 mg, 21%) as an unstable brown solid: 1H NMR δ 8.30 (s, 1H, H-9), 8.25 (s, 1H, H-5), 3.07-3.37 (m, 7H, H-6, H-7, H-8, CH2), 2.36 [s, 6H, N(CH3)2], 1.43 (t, J=7.5 Hz, 3H, CH3); HRMS calcd for C14H18N4O2 (M+) m/z 274.1430, found 274.1428.

1. temperaturecooled to 0° C.
2. stirringThe solution was stirred at 20° C. for 5 h
3. extractionextracted with CHCl3 (3×30 mL)
4. customThe combined organic fraction was dried
5. customthe solvent evaporated
6. customThe residue was purified by column chromatography
7. washeluting with a gradient (0-10%) of MeOH/DCM