Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions

被引：26

作者：

Buden, Maria E. ^{[1
]}

Rossi, Roberto A. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, RA-5000 Cordoba, Argentina

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 49期

关键词：

S(RN)1; phenanthridine; benzophenanthridine; photostimulated reactions;

D O I：

10.1016/j.tetlet.2007.10.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photostimulated reaction of N-(2-halo-benzyl) aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the S(RN)1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo[ a] phenanthridine (98%), and benzo[ c] phenanthridine (84%) were synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8739 / 8742

页数：4

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