Synthesis of 2-substituted 1-benzyl-2,3,4,5-tetrahydro-1-benzazepines by palladium catalysis. Observation of a competitive β-hydride elimination pathway

• Published in: Tetrahedron letters Vol. 44; no. 18; pp. 3675 - 3678
• Main Authors: Qadir, Maryiam, Priestley, Rachael E., Rising, Thomas W.D.F., Gelbrich, Thomas, Coles, Simon J., Hursthouse, Michael B., Sheldrake, Peter W., Whittall, Neil, Hii, K.K.(Mimi)
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.04.2003; Elsevier
• Subjects: benzazepines; Chemistry; Chemistry, Organic; heterocycles; palladium catalysis; Physical Sciences; Science & Technology; β-hydride elimination; benzazepines; palladium catalysis; β-hydride elimination; heterocycles; AMINATION; POTENT; REDUCTION; beta-hydride elimination; PHARMACOLOGY; VASOPRESSIN ANTAGONISTS; RECEPTOR ANTAGONIST
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(03)00676-2

A synthetic route to 1-benzyl-tetrahydro-1-benzazepine is reported, which also permits access to analogous structures with alkyl and aryl substituents at position-2 of the aliphatic ring. Palladium catalysis is utilized in two of the three steps, constructing the seven-membered rings effectively from 2-bromoiodobenzene. Competitive β-hydride elimination was observed in the attempted carbonnitrogen bond formation with a sterically bulky substrate (when R= tert-butyl). Palladium catalysis is utilized in two of the three steps constructing the seven-membered rings effectively from 2-bromo-iodobenzene. Competitive β-hydride elimination was observed in the attempted carbonnitrogen bond formation with a sterically bulky substrate.