1-Oxo-2-hydroxy-1,2-dihydroacronycine: a useful synthon in the acronycine series for the introduction of amino substituents at 6-position and for the conversion into isopropylfuroacridones.
Thermic aromatic nucleophilic displacement of the methoxy group at C-6 of (+/-)-1-oxo-2-hydroxy-1,2-dihydroacronycine (2) by an amine is a reaction that gives a facile entry to acronycine derivatives bearing an amino substituent at this position. The introduction of the amino substituents was confirmed with a long-range 1H-15N correlation NMR spectrum at natural abundance. Under basic conditions, compound 2 can also be rearranged to the corresponding isopropylfuroacridone 12, in 80% yield.
Magiatis
P
P
Laboratory of Pharmacognosy, University of Athens, Greece.
Mitaku
S
S
Skaltsounis
A L
AL
Tillequin
F
F
D000175:Acronine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D000586:Amination; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D007939:Leukemia L1210 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
C450640:1-oxo-2-hydroxy-1,2-dihydroacronycine; D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D000175:Acronine