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

HRID 11163Notes

Reaction equation

HRID 11163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][CH:13]=2.[C:22]1(=[O:28])[NH:26][C:25](=[O:27])[CH:24]=[CH:23]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH:24]2[C:25](=[O:27])[NH:26][C:22](=[O:28])[CH:23]2[C:18]2[C:17]3[CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH2:9]1

Participants

3

Reactant 2

HCID 10935MaleimideHCID 695838952-[2-(2-Chlorophenyl)ethenyl]-5-nitro-1H-indole

Product 1

HCID 219808544-(2-Chlorophenyl)-9-nitro-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dioneYield 74%

Procedure

Reaction of the diene (905) prepared as described in example 455 with maleimide using the procedure described in example 68 gave the adduct (917) (74%) as a dark solid which was immediately aromatised.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-99082dca256848d8960916f5a3b9bcd8
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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