Reacción #11160

Ecuación de reacción

Diene

3-{2-[(E)-2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}propanenitrile

maleimide

→

nitrile

Rendimiento 80.2%

3-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanenitrile

Rendimiento 80.2%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give crude material that
2. 2
   Otrowas chromatographed on silica eluting with ethyl acetate/hexane (1:1)

Procedimiento

Diene (236) (1.30 g, 3.86 mmol) prepared as described in example 96 was reacted with maleimide (0.49 g) following The procedure described in example 68 and then aromatized according to the procedure described in example 70 to give crude material that was chromatographed on silica eluting with ethyl acetate/hexane (1:1). Trituration from methanol gave nitrile (237) (1.33 g, 80%) as a yellow powder, mp 287–288° C. 1H NMR δ [(CD3)2SO] 11.16 (br s, 1H), 8.53 (d, J=2.6 Hz, 1H), 8.02 (s, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.33 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=6.7 Hz, 2H), 3.91 (s, 3H), 3.04 (t, J=6.7 Hz, 2H). Found: C, 65.32; H, 4.15; N, 9.60. C24H16ClN3O3.3/4H2O requires: C, 65.01; H, 3.98; N, 9.47.

Fuente