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Natural product chemistry, part 136: A convenient synthesis of rutacridone and isorutacridone

Naturstoffchemie, 136. Mitt.: Eine kommode Synthese von Rutacridon und Isorutacridon

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

C-alkylation of phenolic acridones with 1,4-dibromo-2-methyl-2-butene under different conditions was studied. Condensations with 1,3 dihydroxy-10-methyl-acridin-9(10H)-one gave an O-alkylated product together with rutacridone and isorutacridone through C-alkylation. The aluminiumoxide and the ion exchange resin method offered the best yields for rutacridone and isorutacridone, respectively. Attempts with 4-hydroxy-10-methylacridin-9(10H)-one yielded several O-alkylated products including a dimer.

Zusammenfassung

Die C-Alkylierung von phenolischen Acridonen mit 1,4-Dibrom-2-methyl-2-buten wurde unter verschiedenen Bedingungen studiert. Die Kondensation mit 1,3-Dihydroxy-10-methylacridin-9(10H)-on ergibt ein O-alkyliertes Produkt zusammen mit Rutacridon und Isorutacridon, die über eine C-Alkylierung entstehen. Die Aluminiumoxid- und die Ionenaustauscher-Methode lieferten die besten Ausbeuten an Rutacridon und Isorutacridon. Versuche mit 4-Hydroxy-10-methyl-acridin-9(10H)-on führten zu einigen O-alkylierten Produkten, darunter ein Dimeres.

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References

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Münster, D-4400, Münster, Federal Republic of Germany

    Johannes Reisch, Anura Wickramasinghe & Wiltrud Probst

Authors
  1. Johannes Reisch
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  2. Anura Wickramasinghe
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  3. Wiltrud Probst
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Reisch, J., Wickramasinghe, A. & Probst, W. Natural product chemistry, part 136: A convenient synthesis of rutacridone and isorutacridone. Monatsh Chem 121, 829–835 (1990). https://doi.org/10.1007/BF00808376

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  • DOI: https://doi.org/10.1007/BF00808376

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