Tetrahedron

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

T Bousquet, JF Fleury, A Daïch, P Netchitaïlo

Index: Bousquet, Till; Fleury, Jean-Francois; Daich, Adam; Netchitailo, Pierre Tetrahedron, 2006 , vol. 62, # 4 p. 706 - 715

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Citation Number: 36

Abstract

An efficient methodology for synthesis of isoindoloisoquinoline and isoindolobenzazepine in oxidized forms as tetracyclic alkaloids cores are reported from N-bromoethylphthalimide () or phthalic anhydride and 2-phenylthioethylamine () 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 ...