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.
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页码：8739 / 8742
页数：4
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