4.5 Article

Rhodium(III)-Catalyzed Annulation of N-Methoxybenzamides with Heterobicyclic Alkenes by C-H Functionalization: Synthesis of Benzo[b]phenanthridinones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 8, Pages 1203-1206

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700029

Keywords

Annulation; C-H activation; Heterocycles; Polycycles; Rhodium

Funding

  1. China Scholarship Council
  2. Alexander von Humboldt Foundation

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A protocol for the rhodium(III)-catalyzed annulation of N-methoxybenzamides with 7-oxa/azabenzonorbornadienes by C-H activation was developed. This method allowed the synthesis of polycyclic products containing an oxygen/nitrogen-bridged structure in excellent yields. The annulated products were successfully transformed into benzo[b] phenanthridinones by a ring-opening/aromatization sequence.

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