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

页码：3675 / 3678

页数：4

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