Arcyriarubin A → 5-Thioxo-3,4-bis(3-indolyl)-3-pyrrolin-2-one

HRID 345664

Reaktionsgleichung

Reaktionsgleichung von HRID 345664
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[C:33](=[O:47])[NH:34][C:35](=O)[C:36]=2[C:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][CH:38]=2)=[CH:24]1>C(COC)OC>[S:10]=[C:35]1[NH:34][C:33](=[O:47])[C:32]([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:23][CH:24]=2)=[C:36]1[C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1

Komponenten

4

Edukt 2

HCID 2399Arcyriarubin AHCID 87949Lawesson's reagent2×

Produkt 1

HCID 187802995-Thioxo-3,4-bis(3-indolyl)-3-pyrrolin-2-oneAusbeute 8,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

820 mg of Lawesson's reagent was added to a solution of 330 mg of 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione in 50 ml of dimethoxyethane and the mixture was heated to reflux for 1 hour. 410 mg of Lawesson's reagent were then added and the mixture was heated to reflux for a further 1 hour. The solvent was evaporated and the residue was purified on silica gel with ethyl acetate/hexane (1:4). Recrystallization from diethyl ether/hexane gave 30 mg of 5-thioxo-3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. 254°-257° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe mixture was heated
  4. temperatureto reflux for a further 1 hour
  5. customThe solvent was evaporated
  6. customthe residue was purified on silica gel with ethyl acetate/hexane (1:4)
  7. customRecrystallization from diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-245fde8cc22e4efda3ade9cfd5a05167
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057614

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