Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using ionic liquid-phase organic synthesis (IoLiPOS) methodology

被引：29
|
作者：
Duchet, Laetitia [1 ]
Legeay, Jean Christophe [1 ]
Carrie, Daniel [1 ]
Paquin, Ludovic [1 ]
Vanden Eynde, Jean Jacques [2 ]
Bazureau, Jean Pierre [1 ]
机构：
[1] Univ Rennes 1, CNRS, UMR 6226, Lab Sci Chim Rennes,Grp Ingn Chim & Mol Vivant IC, F-35042 Rennes, France
[2] Univ Mons, Dept Chim Organ, B-7000 Mons, Belgium
来源：
TETRAHEDRON | 2010年 / 66卷 / 04期
关键词：
Ionic liquid; Liquid phase; 1,2,4-oxadiazole; Bioisostere; O-acylamidoxime; Amidoxime; SUPPORTED SYNTHESIS; EFFICIENT; DISCOVERY; POTENT; AMIDOXIMES; 3,5-DISUBSTITUTED-1,2,4-OXADIAZOLES; OXADIAZOLES; ANTAGONISTS; AGONISTS; SERIES;
D O I：
10.1016/j.tet.2009.11.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New 3,5-disubstituted 1,2,4-oxadiazoles were synthesized in five steps by ionic liquid-phase organic synthesis (IoLiPOS) methodology. The strategy involved the preparation of amidoxime from the ionic liquid-phase bound arylnitrile. Addition of various carboxylic acid to the amidoxime produced the expected 3,5-disubstituted 1,2,4-oxadiazoles via the stable O-acyl amidoxime intermediate grafted on the ionic liquid-phase. The 1,2,4-oxadiazoles were easily cleaved by tran sesterification under mild reaction conditions in high purity with good overall yields. The structures of the intermediates in each step were verified by routine spectroscopic analysis (H-1, C-13 NMR, and HRMS). (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：986 / 994
页数：9
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