Synthesis of tetrahydro-3-benzazepines

Synthesis of Substituted 2,3-Benzodiazepines

“…All of the compounds were derived from the versatile 2-allylbenzaldehyde ( 4 ), which was easily prepared via a three-step synthesis with moderate overall yields by a reaction procedure of O-allylation and Claisen rearrangement followed by O-alkylation. We established the synthetic procedures for substituted benzazepines, including dihydro-1-benzazepines and tetrahydro-3-benzazepines, via the facile, efficient, and high-yield synthetic routes . On the basis of these results, the synthesis of dinitrogen-containing, heterocyclic 2,3-benzodiazepines 1 skeletons from 2-allylbenzaldehyde 2 was our goal (Scheme ).…”

Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines

“…The remarkable biological activity of the 3-benzazepines has stimulated a great variety of synthetic approaches throughout the years. The standard strategies to access to these seven-membered azaheterocycles are based on intramolecular processes such as polar cyclizations, Friedel–Crafts cyclizations, oxidative C–H functionalization-ring expansions, metal-catalyzed Heck cyclizations, or intramolecular hydroamin­(d)­ations . Although each one could be considered relatively useful; indeed, they are very strongly substrate dependent requiring a multistep synthesis of starting materials, which somehow limits the scope of the reactions.…”