Hydrogen Peroxide → HCID 135526561, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 1.0 mL, ca. 20.0 mmol) was added dropwise to a stirred solution of 1-oxide 126 (71 mg, 0.27 mmol) in HOAc (3 mL) at 50° C. and the reaction was stirred at 50° C. for 20 h. The mixture was diluted with aqueous NaHCO3 solution and extracted with DCM (5×50 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-4%) of MeOH/DCM, to give 1,4-dioxide 127 (11 mg, 15%) as a red solid: mp (MeOH/DCM) 153-155° C.; 1H NMR δ 8.10 (s, 1H, H-9), 8.05 (s, 1H, H-5), 7.01 (br s, 1H, NH), 3.69 (d, J=6.5 Hz, 2H, CH2O), 3.59-3.67 (m, 2H, CH2N), 3.15-3.28 (m, 2H, CH2), 2.90-3.03 (m, 2H, CH2), 2.72-2.86 (m, 1H, CH), 1.35 (t, J=7.2 Hz, 3H, CH3), OH not observed; HRMS calcd for C13H16N4O3 (M+) m/z 276.1222, found 276.1222.

Provenance & Evidence