Maleimide → 9-Methoxy-5-phenylpyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

HRID 11143Notes

Reaction equation

HRID 11143 reaction equation
[C:1]1([C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=3)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1(=[O:26])[NH:24][C:23](=[O:25])[CH:22]=[CH:21]1>>[CH3:19][O:18][C:14]1[CH:13]=[CH:12][C:11]2[NH:10][C:9]3[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:8][C:22]4[C:23](=[O:25])[NH:24][C:20](=[O:26])[C:21]=4[C:17]=3[C:16]=2[CH:15]=1

Participants

3

Reactant 2

HCID 10935MaleimideHCID 11844341Methyl 2-(1-phenylvinyl)-1h-indol-5-yl ether

Product 1

HCID 118436889-Methoxy-5-phenylpyrrolo[3,4-c]carbazole-1,3(2h,6h)-dioneYield 73%

Procedure

Reaction of (818) prepared as described in example 418 with maleimide at 180° C. using the procedure described in example 69 gave the adduct (XCVIII; R=phenyl, R′═H) (819), which was used without further purification. The crude Diels-Alder adduct was aromatised with MnO2 using the procedure described in example 79 to give (820) (73%), mp 281–285° C. 1H NMR δ [(CD3)2SO] 11.63 (br s, 1H), 11.15 (br s, 1H), 8.45 (d, J=2.5 Hz, 1H), 7.78–7.76 (m, 2H), 7.68 (s, 1H), 7.65–7.62 (m, 2H), 7.57–7.53 (m, 2H), 7.22 (dd, J=8.8, 2.5 Hz, 1H), 3.89 (s, 3H). Found: C, 72.06; H, 4.57; N, 7.69. C21H14N2O3.1/3H2O requires: C, 72.41; H, 4.24; N, 8.04.

Workup

  1. customprepared
  2. customgave the adduct (XCVIII
  3. customR=phenyl, R′═H) (819), which was used without further purification

Sources & evidence

ORD record
ord-e7283af0700a4001ac72fdbb3ed5f745
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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