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A Synthetic Approach to Perhydro-3-isoquinolinones Bearing an Angular Methyl Group via Organocuprate Addition

Ein Syntheseweg zu Perhydro-3-isochinolinonen mit angulärer Methylgruppe über Organocuprat-Addition

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Summary.

 The addition of organocuprates to the activated C*C double bond in 2H-3,3a,4,5,6,7-hexahydro-2-indenone followed by trapping of the anionic intermediate with MeI as electrophile is reported. Structural assignment of the resulting product was carried out via its oxime using X-ray diffraction. A subsequent Beckmann rearrangement gave the desired title compound.

Zusammenfassung.

 Die Addition von Organocupraten an die aktivierte C*C Doppelbindung in 2H-3,3a,4,5,6,7-Hexahydro-2-indenon, gefolgt von einer Abfangreaktion des anionischen Zwischenprodukts mit MeI als Elektrophil, wurde untersucht. Die Strukturaufklärung des erhaltenen Produktes erfolgte mittels Röntgendiffraktion seines Oxims. Eine anschließende Beckmann-Umlagerung lieferte die gewünschte Titelverbindung.

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Authors and Affiliations

  1.  Institute of Organic Chemistry, Vienna University of Technology, A-1060 Vienna, Austria, AT

    Peter Stanetty, M. Hassan Bahardoust & Marko D. Mihovilovic

  2.  Institute of Mineralogy, Crystallography, and Structural Chemistry, Vienna University of Technology, A-1060 Vienna, Austria, AT

    Kurt Mereiter

Authors
  1. Peter Stanetty
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  2. M. Hassan Bahardoust
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  3. Marko D. Mihovilovic
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  4. Kurt Mereiter
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Additional information

Received March 15, 1999. Accepted May 3, 1999

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Stanetty, P., Bahardoust, M., Mihovilovic, M. et al. A Synthetic Approach to Perhydro-3-isoquinolinones Bearing an Angular Methyl Group via Organocuprate Addition. Monatshefte fuer Chemie 130, 1257–1268 (1999). https://doi.org/10.1007/PL00010187

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  • DOI: https://doi.org/10.1007/PL00010187

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