反应详情

温度

20 °C

A mixture of the 9-hydroxy-4-[2-(methylsulfanyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (508) (34.5 mg, 0.092 mmol), prepared according to example 25, and 2-phenylsulfonyl-3-phenyloxaziridine (Davis reagent) (26.5 mg, 0.102 mmol) in THF (10 mL) was stirred at 20° C. for 2.5 h, then adsorbed directly onto silica gel and chromatographed. Elution with 0–3% MeOH/CH2Cl2 then 3–4% MeOH/CH2Cl2 gave (after crystallisation from THF/CH2Cl2/pentane) the 9-Hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (510) (I; Ar=2-(methylsulfinyl)phenyl) in a 86% yield as a yellow solid; mp 321–323° C. 1H NMR [(CD3)2SO] δ 11.86, 11.85 (2br s, 1H), 11.09 (br s, 1H), 9.30 (br s, 1H), 8.32 (d, J=2.4 Hz, 1H), 8.04, 7.97 (2d, J=7.6 Hz, 1H), 7.74 (t, J=7.6 Hz, 1H), 7.65, 7.62 (2t, J=7.4 Hz, 1H), 7.62, 7.54 (2s, 1H), 7.47 (d, J=9.1 Hz, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.09 (dd, J=8.7, 2.5 Hz, 1H), 2.43, 2.31 (2s, 3H). Found: C, 64.60; H, 3.88; N, 6.87. C21H14N2O4S requires C, 64.61; H, 3.61; N, 7.18.

1. customprepared
2. customchromatographed
3. washElution with 0–3% MeOH/CH2Cl2
4. custom3–4% MeOH/CH2Cl2 gave
5. custom(after crystallisation from THF/CH2Cl2/pentane) the 9-Hydroxy-4-[2-(methylsulfinyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (510) (I; Ar=2-(methylsulfinyl)phenyl) in a 86% yield as a yellow solid