Oxidized isoquinolinoisoindolinone and benzazepinoisoindolinone alkaloids cores by convergent cyclisation processes: π-aromatic attack of thionium and oxonium species

  • Bousquet T
  • Fleury J
  • Daïch A
 et al. 
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An efficient methodology for synthesis of isoindoloisoquinoline 5a and isoindolobenzazepine 5b in oxidized forms as tetracyclic alkaloids cores are reported from N-bromoethylphthalimide (6) or phthalic anhydride and 2-phenylthioethylamine (8) in a five- or six-step sequence, respectively, in overall very good yields. The key step of this methodology is based on an intramolecular π-cationic cyclization of the thionium ion species. Alternatively, another four-step route was explored and based in an ultimate step on the cyclodehydration of an aldehyde functionality, which used as intermediate in the latest strategy, via the oxonium ion cation.

Author-supplied keywords

  • Alkaloid
  • Benzazepine
  • Cyclization
  • Isoindole
  • Isoquinoline
  • N-Acyliminium ion
  • Oxonium ion
  • Pummerer
  • Thionium ion
  • α-Amidoalkylation

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