2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(3,4-Methylenedioxy-phenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl-]-4-hydoxy-2,3,4,9-tetrahydro-1H-beta-carboline

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Reaktionsgleichung

C(C1C(=O)C(Cl)=C(Cl)C(=[O:6])C=1C#N)#N.[CH2:15]1[O:23][C:22]2[CH:21]=[CH:20][C:19]([CH:24]3[C:36]4[NH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[C:28]=4[CH2:27][CH2:26][N:25]3[C:37]3[N:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47]C(OC)=C(OC)C=4)=[CH:39][N:38]=3)=[CH:18][C:17]=2[O:16]1.[CH2:53]1[CH2:57][O:56][CH2:55][CH2:54]1.O>C(OCC)(=O)C>[CH2:15]1[O:23][C:22]2[CH:21]=[CH:20][C:19]([CH:24]3[C:36]4[NH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[C:28]=4[CH:27]([OH:6])[CH2:26][N:25]3[C:37]3[N:38]=[CH:39][C:40]([C:43]4[CH:54]=[CH:53][C:57]([O:56][CH3:55])=[CH:47][CH:48]=4)=[CH:41][N:42]=3)=[CH:18][C:17]=2[O:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of DDQ (113.5 mg, 0.5 mmol) and 1-(3,4-methylenedioxyphenyl)-2-[5-(3,4-dimethoxyphenyl)pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline (prepared as in Example 3) (51 mg, 0.1 mmol) was added a mixed solvent of THF:water (9:1) at −78° C. The mixture was stirred at 0° C. and allowed to warm to room temperature over a period of 15 h. Column chromatography (silica gel, hexanes:ethyl acetate=1:1) yielded the-oxo- and -hydroxy derivatives respectively, as white solids.

Aufarbeitung

temperatureto warm to room temperature over a period of 15 h

Quellen und Nachweise

ORD-Eintrag: ord-4f2fa12b1b6b46efaa49296db3acb482
Quelldatensatz: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06492358B2

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