NHC-Catalyzed Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes

1,2,4-Oxadiazoles are key scaffolds in natural products and bioactive molecules. This study reports an efficient NHC-catalyzed [4 + 1] cyclization from accessible aldehydes and amidoximes to build it, concisely synthesizing tioxazafen, ataluren, and an mGluR5 antagonist. Broad substrate scope and gram-scale transformations confirm efficiency and practicality.

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Publication Details

Journal
Organic Letters
Published
2025-11-11
DOI
https://doi.org/10.1021/acs.orglett.5c04219
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
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article

NHC-Catalyzed Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes

Zhenqian Fu, Haibin Zhu
Organic Letters
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

NHC-Catalyzed Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes

Zhenqian Fu, Haibin Zhu
article en

Abstract

1,2,4-Oxadiazoles are key scaffolds in natural products and bioactive molecules. This study reports an efficient NHC-catalyzed [4 + 1] cyclization from accessible aldehydes and amidoximes to build it, concisely synthesizing tioxazafen, ataluren, and an mGluR5 antagonist. Broad substrate scope and gram-scale transformations confirm efficiency and practicality.

Organic LettersVol. 27(46)
Nanjing Tech University (CN), The Synergetic Innovation Center for Advanced Materials (CN)
Openalex Percentile: Top 74%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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