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.

引用

页码：6433 / 6448

页数：16

共 31 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .10. THE DECARBOXYLATIVE ROUTE TO AZOMETHINE YLIDES - BACKGROUND AND RELEVANCE TO PYRIDOXAL DECARBOXYLASES
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[3] IMINIUM ION ROUTE TO AZOMETHINE YLIDES FROM PRIMARY AND SECONDARY-AMINES
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[5] TANDEM INTRAMOLECULAR MICHAEL ADDITION AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF OXIMES - VERSATILE NEW CARBON CARBON BOND FORMING METHODOLOGY
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[6] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLO-ADDITIONS OF ALPHA-AMINO-ACID ESTERS - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES
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[7] [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT
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[9] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .23. MECHANISMS OF THE REACTIONS OF NINHYDRIN AND PHENALENE TRIONE WITH ALPHA-AMINO-ACIDS - X-RAY CRYSTAL-STRUCTURE OF PROTONATED RUHEMANNS PURPLE, A STABLE AZOMETHINE YLIDE
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[10] DECARBOXYLATION OF ALPHA-AMINO-ACIDS BY PYRUVIC-ACID AND ITS DERIVATIVES - EVIDENCE FOR AZOMETHINE YLIDES IN INVITRO ANALOGS OF PYRUVOYL ENZYMIC PROCESSES
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