A versatile solid-phase synthesis of 3-aryl-1,2,4-oxadiazolones and analogues

被引：17

作者：

Charton, Julie

Cousaert, Nicolas

Bochu, Christophe

Willand, Nicolas

Deprez, Benoit ^{[1
]}

Deprez-Poulain, Rebecca

机构：

[1] INSERM, U761 Biostruct & Drug Discovery, F-59006 Lille, France

[2] Univ Lille, Fac Pharm, F-59006 Lille, France

[3] Inst Pasteur, F-59000 Lille, France

[4] LARMN, UMR 8009, CNRS, F-59006 Lille, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 08期

关键词：

acidic heterocycles; solid phase; Mitsunobu reaction; attachment; cleavage; Sonogashira coupling;

D O I：

10.1016/j.tetlet.2006.12.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here the first method to load acidic heterocyclic compounds (1, 2,4-oxadiazol-5-one, 1,2,4-oxadiazol-5-thione and 1,2,3,5-oxathiadazol-2-oxide) on a polymer. Using Mitsunobu conditions, these heterocycles were anchored on a 4-hydroxymethyl-3-methoxyphenoxybutyric acid benzhydrylamine (HMPB-BHA) resin. After diversification, compounds can be recovered by a simple treatment in diluted TFA. To illustrate the utility of this procedure, iodophenyl derivatives were anchored on the same resin. A HRMAS-NMR analysis shed light on the reactivity of these heterocycles in Mitsunobu conditions. A subsequent diversification using a Sonogashira coupling produced a small array of novel (arylethynyl)-phenyl-1, 2,4-oxadiazol-5-ones. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1479 / 1483

页数：5