A stereospecific synthesis of tetra-substituted chiral piperazines

被引:14
作者
Abdel-Jalil, RJ [1 ]
Al-Qawasmeh, RA [1 ]
Al-Abed, Y [1 ]
Voelter, W [1 ]
机构
[1] Univ Tubingen, Inst Physiol Chem, Phys Biochem Abt, D-72076 Tubingen, Germany
关键词
anhydro sugars; piperazine derivatives; chiral piperazines;
D O I
10.1016/S0040-4039(98)01677-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one pot reaction of the epoxy triflates 1 or 2 with a variety of N,N'-disubstituted ethylenediamines yields the corresponding chiral piperazine derivatives 3a-e and 4a-e of potential pharmacological interest in high yields, (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7703 / 7704
页数:2
相关论文
共 13 条
[1]  
ALABED Y, 1992, TETRAHEDRON LETT, V33, P3305
[2]   Pyridinium ions adjacent to oxirane rings: Useful intermediates for the stereospecific synthesis of beta-hydroxy ketones [J].
AlAbed, Y ;
Naz, N ;
Khan, KM ;
Voelter, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (05) :523-524
[3]   4-O-TfO-2,3-anhydro-beta-L-ribopyranosides as chiron: A formal synthesis of canadensolide [J].
AlAbed, Y ;
Naz, N ;
Mootoo, D ;
Voelter, W .
TETRAHEDRON LETTERS, 1996, 37 (48) :8641-8642
[4]   STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES [J].
ALABED, Y ;
ALTEL, TH ;
VOELTER, W .
TETRAHEDRON, 1993, 49 (41) :9295-9306
[5]   ENHANCED D-1 AFFINITY IN A SERIES OF PIPERAZINE RING-SUBSTITUTED 1-PIPERAZINO-3-ARYLINDANS WITH POTENTIAL ATYPICAL ANTIPSYCHOTIC ACTIVITY [J].
BOGESO, KP ;
ARNT, J ;
FREDERIKSEN, K ;
HANSEN, HO ;
HYTTEL, J ;
PEDERSEN, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (22) :4380-4392
[6]   STRUCTURE-ACTIVITY-RELATIONSHIPS IN PRAZOSIN-RELATED COMPOUNDS .2. ROLE OF THE PIPERAZINE RING ON ALPHA-BLOCKING ACTIVITY [J].
GIARDINA, D ;
GULINI, U ;
MASSI, M ;
PILONI, MG ;
POMPEI, P ;
RAFAIANI, G ;
MELCHIORRE, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (06) :690-698
[7]  
Giardina D, 1996, ARZNEIMITTELFORSCH, V46, P1054
[8]   Structure-activity relationships of a series of substituted benzamides: Potent D-2/5-HT2 antagonists and 5-HT1a agonists as neuroleptic agents [J].
Norman, MH ;
Rigdon, GC ;
Hall, WR ;
Navas, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1172-1188
[9]   Syntheses of new pyridonecarboxylic acid derivatives containing 1- or 2-naphthyl substituents at N-1 and their anti-HIV-RT activities [J].
Oh, YS ;
Cho, SH .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (01) :17-23
[10]   SYNTHESIS AND VASODILATOR ACTIVITY OF NEW PIPERAZINE DERIVATIVES [J].
REGNIER, GL ;
CANEVARI, RJ ;
LAUBIE, MJ ;
LEDOUARE.JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (06) :1151-&