Synthesis of 2-substituted 1-benzyl-2, 3, 4, 5-tetrahydro-1-benzazepines by palladium catalysis. Observation of a competitive β-hydride elimination pathway
…, T Gelbrich, SJ Coles, MB Hursthouse, PW Sheldrake…
Index: Qadir, Maryiam; Priestley, Rachael E.; Rising, Thomas W. D. F.; Gelbrich, Thomas; Coles, Simon J.; Hursthouse, Michael B.; Sheldrake, Peter W.; Whittall, Neil; Hii Tetrahedron Letters, 2003 , vol. 44, # 18 p. 3675 - 3678
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Citation Number: 31
Abstract
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 ...