The syntheses of the (indolyl)quinazolines (VIII) and (XIII) proceed via two key steps. The first one involves the intramolecular cyclization of the cinnamic acid esters (IV). The ring closure of ester (IVb) does not occur regiospecifically but affords a mixture of two indole carboxylic esters. The second key step is based on a chemoselective and regioselective hetarylation reaction: indolyl-magnesium compounds are reacted with chloroquinazolines like (VII) to yield the targets (VIII) and (XIII). These compounds are relatively potent inhibitors of EGFR-TK. In addition, compound (XIII) can also be viewed as HER-2-tyrosine kinase inhibitor. Moreover, the new class shows remarkable strong fluorescence properties. -(LUETH*, A.; LOEWE, W.; Eur.

An Aminoisoflavone -Salicyloylindole Ring Transformation. -Nitroisoflavones are precursors of aminoisoflavones are prepared from different starting materials 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.

Die Sulfinsäure (I) reagiert mit Acetanhydrid/Eisessig unter Disproportionierung zu einem Gemisch der Sulfonsäure (II) und des Thiosulfonsäureesters (III).

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Chromon‐3‐carbaldehyd (I) wird mit Formamidin (II) zu Acylpyrimidin (III) und zum 5‐Hydroxy‐benzopyrano‐pyrimidin‐Derivat (IV) umgesetzt, von denen das letztere mit Chrom(VI)‐ oxid in Pyridin zum Lacton (V) oxidiert wird.