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2004
Indole derivatives
R 0140
An Aminoisoflavone — Salicyloylindole Ring Transformation. — Nitroisoflaare precursors of aminoisoflavones are prepared from different starting materials
44- 125 vones
via acetic acid derivatives such as (I). The reduction of the nitroisoflavones is carried
out by using either palladium on carbon in the presence of cyclohexene or by zinc dust.
Surprisingly, reduction of nitroisoflavones (VI) affords only the salicyloylindoles (VII)
instead of the expected aminoisoflavones. Reduction of flavone (VIII) yields both the
N-alkylated salicyloylindole (XI) as well as the corresponding aminoisoflavone (IX),
depending on the reaction time. Isoflavylium acetate (XII) is transformed into aminoisoflavone (XIII) as a sole product after 30 minutes. Prolonged reduction time furnishes additionally the salicyloylindole (XIV). A mechanism for the ring transformation is postulated. — (LOEWE*, W.; WITZEL, S.; TAPPMEYER, S.; ALBUSCHAT,
R.; J. Heterocycl. Chem. 41 (2004) 3, 317-326; Inst. Pharm., FU Berlin, D-14195
Berlin, Germany; Eng.) — H. Hoennerscheid
2004
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