Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli Cyclization/Michael Addition Sequence

Shengdong Wang (1) , Régis Guillot (1) , Jean-François Carpentier (2) , Yann Sarazin (2) , Christophe Bour (1) , Vincent Gandon (1) , David Lebœuf (1)

1 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
2 ISCR - Institut des Sciences Chimiques de Rennes

Herein, we report the preparation of bridged tetrahydrobenzo[b]azepines, which was accomplished through an aza-Piancatelli cyclization/Michael addition sequence in a one-pot fashion from readily available precursors. It is noteworthy that a general method to access these scaffolds was hitherto unprecedented. Additionally, the multifaceted aspects of this process have been exemplified through its application to the synthesis of 2-azabicyclo[3.2.1]octanes and bridged tetrahydrobenzo[b]oxepines, along with post-derivatizations.

Keywords: Lewis acid; medium-size N-heterocycles; tetrahydrobenzo[b]azepines; electrocyclization; hexafluoroisopropanol

Domains: Chemical Sciences

Shengdong Wang, Régis Guillot, Jean-François Carpentier, Yann Sarazin, Christophe Bour, et al.. Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli Cyclization/Michael Addition Sequence. Angewandte Chemie International Edition, 2020, 59 (3), pp.1134-1138. ⟨10.1002/anie.201911761⟩. ⟨hal-02438534⟩