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Heterocyclically bridged tricyclic β-lactames: A simple synthesis of 1,2,2a,8a-tetrahydro-3-oxa-1-aza-cyclobuta[b]naphthalen-2-ones

Heteroüberbrückte tricyclische β-Lactame: Ein einfacher Zugang zu 1,2,2a,8a-Tetrahydro-3-oxa-1-aza-cyclobuta[b]naphthalin-2-onen

  • Organische Chemie Und Biochemie
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Summary

The tricyclic 3,4-bridged β-lactames7 and8 containing a hetero atom as 3-substituent of the azetidin-2-one ring were synthesized by intramolecular radical cyclization usingcis-substituted 3-(2-bromo-aryloxy)-azetidine-2-ones6 as precursors. These precursors were generated by stereospecific acid chloride-imine reaction from the corresponding substituted (2-bromophenoxy)-acetic acid chlorides2 and imine5.

Zusammenfassung

Die cis-substituierten 3-(2-Bromaryloxy)-azetidin-2-one6, dargestellt durch stereospezifische Säurechlorid/Imin-Reaktion aus den entsprechenden (2-Brom-phenoxy)-acetylchloriden2 und den Iminen5, reagieren im Zuge einer intramolekularen radikalischenexo-trig-Reaktion zu den 3,4-heteroüberbrückten tricyclischen β-Lactamen7 und8.

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Authors and Affiliations

  1. Institut für Organische Chemie, Leopold-Franzens-Universität Innsbruck, A-6020, Innsbruck, Austria

    A. Takó & K. -H. Ongania

  2. Institut für Anorganische, Allgemeine und Theoretische Chemie, Leopold-Franzens-Universität Innsbruck, A-6020, Innsbruck, Austria

    K. Wurst

Authors
  1. A. Takó
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  2. K. -H. Ongania
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  3. K. Wurst
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Takó, A., Ongania, K.H. & Wurst, K. Heterocyclically bridged tricyclic β-lactames: A simple synthesis of 1,2,2a,8a-tetrahydro-3-oxa-1-aza-cyclobuta[b]naphthalen-2-ones. Monatsh Chem 128, 1149–1156 (1997). https://doi.org/10.1007/BF00807565

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  • DOI: https://doi.org/10.1007/BF00807565

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