反应 #11224

反应方程式

anhydride

4-(2-Chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydro-1H-furo[3,4-c]carbazole-1,3(3aH)-dione

2,4-dimethoxybenzylamine

→

4-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

溶剂

acetic acid

反应条件

后处理

1. 1
   温度The resulting solution was heated
2. 2
   温度at reflux for 6 hours
3. 3
   浓缩before being partially concentrated under reduced pressure
4. 4
   workup.ADDITIONdiluted with water
5. 5
   其他to precipitate an orange solid, which
6. 6
   过滤was collected by filtration
7. 7
   洗涤washed with water
8. 8
   其他dried in vacuo
9. 9
   workup.DISSOLUTIONThis crude material was then dissolved in p-dioxane
10. 10
    其他before being chromatographed on silica eluting with ethyl acetate/hexane (1:1)
11. 11
    其他Crystallisation from methanol

实验过程

To a solution of anhydride (286) (2.80 g, 7.42 mmol) prepared as described in example 296 in glacial acetic acid (70 mL) was added 2,4-dimethoxybenzylamine (1.67 mL, 11.1 mmol). The resulting solution was heated at reflux for 6 hours before being partially concentrated under reduced pressure and diluted with water to precipitate an orange solid, which was collected by filtration, washed with water and dried in vacuo. This crude material was then dissolved in p-dioxane and aromatized according to the procedure for example 79, before being chromatographed on silica eluting with ethyl acetate/hexane (1:1). Crystallisation from methanol then gave carbazole (287) (1.46 g, 37%) as a yellow powder, mp 224–226° C. 1H NMR δ [(CD3)2SO] 12.02 (br s, 1H), 8.45 (d, J=2.6 Hz, 1H), 7.62 (s, 1H), 7.58 (m, 2H), 7.53–7.42 (m, 3H), 7.25 (dd, J=8.8, 2.6 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.57 (d, J=2.3 Hz, 1H), 6.45 (dd, J=8.4, 2.3 Hz, 1H), 4.68 (s, 2H), 3.88 (s, 3H), 3.80 (s, 3H), 3.72 (s, 3H). Found: C, 68.22; H, 4.37; N, 5.29. C30H23ClN2O5 requires: C, 68.38; H, 4.40; N, 5.32.

来源