AMINATION OF ESTER ENOLATES WITH ORTHO-(2,4-DINITROPHENYL)HYDROXYLAME

被引：32

作者：

RADHAKRISHNA, AS

LOUDON, GM

MILLER, MJ

机构：

[1] PURDUE UNIV,SCH PHARM & PHARM SCI,DEPT MED CHEM & PHARMACOGNOSY,W LAFAYETTE,IN 47907

[2] UNIV NOTRE DAME,DEPT CHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enolates derived from diethyl malonate and its 2-substituted analogues aminate in good yield with O-(2, 4-dinitrophenyl)hydroxylamine (1) as an amino-transfer reagent. The 2-aminomalonates thus produced are readily converted to the corresponding amino acids by hydrolysis and decarboxylation. As the ester enolates become more basic, less amino-group transfer is observed, although the aminating reagent 1 is converted to. © 1979, American Chemical Society. All rights reserved.

引用

收藏

页码：4836 / 4841

页数：6

相关论文

共 33 条

[1] KETENE ALKYLTRIALKYLSILYL ACETALS - SYNTHESIS, PRYOLYSIS AND NMR STUDIES [J].

AINSWORTH, C ;

CHEN, F ;

KUO, YN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (01) :59-+

[2] HYDROLYSIS OF CHLORAMINE IN ALKALINE SOLUTION [J].

ANBAR, M ;

YAGIL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (10) :1790-&

[3] ELECTROPHILIC AMINATION OF CARBANIONS WITH N,N-DIALKYL-O-ARYLSULFONYLHYDROXYLAMINES [J].

BOCHE, G ;

MAYER, N ;

BERNHEIM, M ;

WAGNER, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (09) :687-688

[4] ALKYL EFFECTS ON EQUILIBRIUM ACIDITIES OF CARBON ACIDS IN PROTIC AND DIPOLAR APROTIC MEDIA AND IN GAS-PHASE [J].

BORDWELL, FG ;

BARTMESS, JE ;

HAUTALA, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (16) :3095-3101

[5] REACTION OF ORGANOBORANES WITH CHLORAMINE + WITH HYDROXYLAMINE-O-SULFONIC ACID . CONVENIENT SYNTHESIS OF AMINES FROM OLEFINS VIA HYDROBORATION [J].

BROWN, HC ;

BREUER, E ;

MURPHY, WS ;

HEYDKAMP, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (17) :3565-&

[6] PURPUROGALLIN .3. SYNTHESIS OF PURPUROGALLIN AND SOME ANALOGUES [J].

CAUNT, D ;

CROW, WD ;

HAWORTH, RD ;

VODOZ, CA .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (JUN) :1631-1635

[7] SYNTHESIS OF CARBAMATES OF ALPHA-AMINO SULFONAMIDES [J].

GILMORE, WF ;

LIN, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (23) :4535-4537

[8]

Hartung W. H., 1973, ORG SYNTH, VV, P376

[9] SYNTHESIS OF OPTICALLY-ACTIVE SULFOXIMINES FROM OPTICALLY-ACTIVE SULFOXIDES [J].

JOHNSON, CR ;

KIRCHHOF.RA ;

CORKINS, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2458-2459

[10] PRIMARY AND SECONDARY IONIZATIONS OF ALPHA HYDROGENS OF PHENYLACETONITRILE BY N-BUTYLLITHIUM [J].

KAISER, EM ;

HAUSER, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (10) :2348-&

← 1 2 3 4 →