PREPARATION OF NOVEL LIPOPHILIC GABA ANALOGS CONTAINING CYCLOPROPANE RINGS VIA CYCLOPROPANATION OF N-SILYLATED UNSATURATED AMINES

被引：21

作者：

PAULINI, K

REISSIG, HU

机构：

[1] TECH UNIV DRESDEN,INST ORGAN CHEM,D-01062 DRESDEN,GERMANY

[2] TH DARMSTADT,INST ORGAN CHEM,DARMSTADT,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1995年 / 337卷 / 01期

关键词：

D O I：

10.1002/prac.19953370112

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Novel lipophilic gamma-amino acids 8 and 9 analogous to GABA containing cyclopropane rings are synthesized by Rh(II)-catalyzed reaction of diazo compounds 2 and 3 with N,N-bis(trimethylsilyl)allylamine (1) and subsequent hydrolysis. In addition, routes are described leading to the vinylogous GABA analogue 15 and to the unusual tricyclic gamma-amino acid 20.

引用

页码：55 / 59

页数：5

共 27 条

[1] [1,4] AND [5,5] THERMAL SIGMATROPIC REARRANGEMENTS OF 2-PENTADIENYLOXYPYRIDINE N-OXIDES
ALKER, D
OLLIS, WD
SHAHRIARIZAVAREH, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1637 - 1643
[2] HIGH-AFFINITY ANALOGS OF NEUROPEPTIDE-Y CONTAINING CONFORMATIONALLY RESTRICTED NON-PROTEINOGENIC AMINO-ACIDS
BECKSICKINGER, AG
HOFFMAN, E
PAULINI, K
REISSIG, HU
WILLIM, KD
WIELAND, HA
JUNG, G
[J]. BIOCHEMICAL SOCIETY TRANSACTIONS, 1994, 22 (01) : 145 - 149
[3] BOWERY NG, 1990, GABA BETA RECEPTORS
[4] ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN
BURGESS, LE
MEYERS, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) : 9858 - 9859
[5] MECHANISM OF INACTIVATION OF GAMMA-AMINOBUTYRIC-ACID AMINOTRANSFERASE BY 4-AMINO-5-HEXYNOIC ACID (GAMMA-ETHYNYL GABA)
BURKE, JR
SILVERMAN, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9329 - 9340
[6] CIGANEK E, 1970, J ORG CHEM, V56, P862
[7] USES OF SI-N BONDS IN ORGANIC-SYNTHESIS - A DIRECT SYNTHESIS OF FUNCTIONAL PROTECTED PROPARGYLIC PRIMARY AMINES
CORRIU, RJP
HUYNH, V
MOREAU, JJE
[J]. TETRAHEDRON LETTERS, 1984, 25 (18) : 1887 - 1890
[8] VIGABATRIN - A REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES, AND THERAPEUTIC POTENTIAL IN EPILEPSY AND DISORDERS OF MOTOR CONTROL
GRANT, SM
HEEL, RC
[J]. DRUGS, 1991, 41 (06) : 889 - 926
[9] HUSSAIN R, 1991, LIEBIGS ANN CHEM, P963
[10] SYNTHESIS OF GAMMA-AMINOBUTYRIC ACID ANALOGS OF RESTRICTED CONFORMATION .2. THE 2-(AMINOMETHYL)CYCLOALKANECARBOXYLIC ACIDS
KENNEWELL, PD
MATHARU, SS
TAYLOR, JB
WESTWOOD, R
SAMMES, PG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11): : 2563 - 2570

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