Synthetic preparation of Ataluren via a one-pot synthesis of 1,2,4-oxadiazoles employing a DMAP catalyzed amidoxime O-acylation/cyclization pathway

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-09-02 DOI:10.1080/00397911.2025.2548309

Austin Carter (Data curation Methodology Writing – review & editing) , Daniel Wright (Data curation Methodology) , Giavanna Alongi (Data curation) , Christopher G. Hamaker (Data curation) , Shawn R. Hitchcock (Conceptualization Funding acquisition Methodology Project administration Supervision Writing – original draft) , Desmond H. Murray (Conceptualization Data curation Methodology Writing – review & editing)

引用次数: 0

Abstract

The drug ataluren has been prepared using a one-pot synthesis of 1,2,4-oxadiazoles from amidoximes. This one-pot approach involves the in situ formation of O-acylamidoximes via the DMAP catalyzed O-acylation of amidoximes followed by cyclization in the presence of potassium hydroxide in DMSO. Using this methodology, a series of 17 examples of 1,2,4-oxadiazoles were formed in isolated yields up to 94% and the synthesis of ataluren was completed.

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采用DMAP催化偕胺肟o -酰化/环化途径，一锅法合成1,2,4-恶二唑合成阿特鲁酮

以偕胺肟为原料，采用一锅法合成1,2,4-恶二唑，制备了药物阿塔卢酮。这种一锅法是通过DMAP催化偕胺肟的o -酰化，然后在DMSO中氢氧化钾存在下进行环化，原位形成o -酰基胺肟。用该方法合成了17个1,2,4-恶二唑，分离收率高达94%，完成了阿塔卢酮的合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.