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

被引：49
|
作者：
Qadir, M
Priestley, RE
Rising, TWDF
Gelbrich, T
Coles, SJ
Hursthouse, MB
Sheldrake, PW
Whittall, N
Hii, KK [1 ]
机构：
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
[2] Univ Southampton, EPSRC, Natl Xray Crystallog Serv, Southampton SO17 1BJ, Hants, England
[3] GlaxoSmithKline Inc, Tonbridge TN11 9AN, Kent, England
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 18期
关键词：
palladium catalysis; heterocycles; benzazepines; beta-hydride elimination;
D O I：
10.1016/S0040-4039(03)00676-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 P-hydride elimination was observed in the attempted carbon-nitrogen bond formation with a sterically bulky substrate (when R = tert-butyl). (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3675 / 3678
页数：4
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