Furil → (z)-7,9-Dihydro-2,3-di-(2-furanyl)-9-[(3-methoxy-1h-pyrrol-2-yl)methylene]-8h-pyrrolo[3,2-f]quinoxalin-8-one

HRID 324963Notes

Reaction equation

HRID 324963 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:13]/[C:14]1[NH:15][CH:16]=[CH:17][C:18]=1[O:19][CH3:20])/[C:5](=[O:12])[NH:6]2.[CH:21]1[CH:25]=[C:24]([C:26]([C:28]([C:30]2[O:34][CH:33]=[CH:32][CH:31]=2)=O)=O)[O:23][CH:22]=1>C(O)C>[O:23]1[CH:22]=[CH:21][CH:25]=[C:24]1[C:26]1[C:28]([C:30]2[O:34][CH:33]=[CH:32][CH:31]=2)=[N:11][C:10]2[CH:9]=[CH:8][C:7]3[NH:6][C:5](=[O:12])/[C:4](=[CH:13]\[C:14]4[NH:15][CH:16]=[CH:17][C:18]=4[O:19][CH3:20])/[C:3]=3[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 68119FurilHCID 15512603(Z)-4,5-diamino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 9823655(z)-7,9-Dihydro-2,3-di-(2-furanyl)-9-[(3-methoxy-1h-pyrrol-2-yl)methylene]-8h-pyrrolo[3,2-f]quinoxalin-8-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using Method A above, (Z)-4,5-diamino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (60 mg, 0.22 mmol) (Starting Material 5) was condensed with furil (200 mg) (Aldrich) in ethanol (3 mL) at reflux to give (Z)-7,9-dihydro-2,3-di-(2-furanyl)-9-[(3-methoxy-1H-pyrrol-2-yl)methylene]-8H-pyrrolo[3,2-f]quinoxalin-8-one in 86% yield.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-94a7466fb48c4d76a5fd8e43fbe96a7a
Source dataset
uspto-grants-2001_04
Patent number
US06221867B1

Reaction notes

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