The reaction of phthalidylidene dichloride with primary amines. Synthesis and X-ray molecular structure of N-substituted phthalisoimides

被引：10
|
作者：
Guirado, A [1 ]
Zapata, A [1 ]
de Arellano, MCR [1 ]
机构：
[1] UNIV MURCIA, FAC QUIM, DEPT QUIM INORGAN, E-30071 MURCIA, SPAIN
来源：
TETRAHEDRON | 1997年 / 53卷 / 14期
关键词：
D O I：
10.1016/S0040-4020(97)00194-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of N-substituted phthalisoimides, by reaction of phthalidylidene dichloride with primary amines, is described. The reactions with arylamines, arylenediamines and alkylenediamines lead to the corresponding phthalisoimides or bisphthalisoimides in nearly quantitative yields. However, the reactions with alkylamines are not useful because of the relatively high nucleophilicity of alkylamines. Certain particular behaviours of arylamines, associated with the presence of specific ortho-substituents have been found. The reactions of arylamines bearing an o-hydroxymethyl group provide a convenient method for preparing 2-benzoxazinylbenzoic acids. The X-ray crystallographic structures of N-(2-methoxyphenyl)phthalisoimide 3a and 2-(4H-3,1-benzoxazin-2-yl)benzoic acid 15a have been determined. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：5305 / 5324
页数：20
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