Bromination and iodination of 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine:: A convenient entry to unsymmetrical analogs of Troger's base

被引：30

作者：

Didier, Delphine ^{[1
]}

Sergeyev, Sergey ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Polymeres, CP 206-01,Blvd Du Triomphe, B-1050 Brussels, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 23期

关键词：

heterocycles; electrophilic substitution; Troger's base; bromination; lodination;

D O I：

10.1002/ejoc.200700253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine can easily be prepared from aniline and paraformaldehyde. Its reactions with either N-bromosuccinimide (NBS) or with iodine monochloride (ICI) in the presence of a suitable activator smoothly afford 2-bromo- and 2-iodo- derivatives, respectively. The combination of these halogenation methods provides access to the 8-bromo-2-iodo derivative, which is an interesting and otherwise inaccessible intermediate for the synthesis of unsymmetrical analogs of Troger's base. The reported halogenations represent the first examples of electrophilic substitution in 6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：3905 / 3910

页数：6

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