X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .28. THE IMINIUM ION ROUTE TO AZOMETHINE YLIDES - BACKGROUND AND REACTION OF AMINES WITH BIFUNCTIONAL KETONES

被引：73

作者：

ARDILL, H

DORRITY, MJR

GRIGG, R

LEONLING, MS

MALONE, JF

SRIDHARAN, V

THIANPATANAGUL, S

机构：

[1] UNIV LEEDS,DEPT CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

[3] SILPAKORN UNIV,FAC SCI,DEPT CHEM,NAKHON PATHOM 73000,THAILAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)96013-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of isatin, ninhydrin and acenaphthenequinone with primary and secondary amines gives rise to stereospecific formation of intermediate azomethine ylides which can be trapped by cycloaddition to methyl acrylate or N-methylmaleimide. The regiochemistry of the cycloadditions to methyl acrylate is controlled by both frontier orbital and steric interactions with the latter dominating in the examples studied. © 1990.

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页码：6433 / 6448

页数：16

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