Maleimide → 4-(3,5-Dinitrophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione

HRID 11043

Reaction equation

HRID 11043 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=[CH:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([N+:23]([O-:25])=[O:24])[CH:15]=1)=[CH:6]2.[C:26]1(=[O:32])[NH:30][C:29](=[O:31])[CH:28]=[CH:27]1>>[N+:20]([C:18]1[CH:19]=[C:14]([CH:13]2[CH:28]3[C:29](=[O:31])[NH:30][C:26](=[O:32])[CH:27]3[C:6]3[C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH2:12]2)[CH:15]=[C:16]([N+:23]([O-:25])=[O:24])[CH:17]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 10935MaleimideHCID 867601905-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole

Product 1

HCID 867601894-(3,5-Dinitrophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dioneYield 89%

Procedure

The reaction of 5-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole (II; Ar=3,5-dinitrophenyl) (40) prepared as described in example 46 with maleimide using the procedure described in example 69 gave 4-(3,5-Dinitrophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=3,5-dinitrophenyl, R10═H) (41) in a 89% yield as a glassy solid which was used without further purification.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-c3b23bced8d541d3b1f3575920f404ea
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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