One-Pot Method to Access 1,3,4-Oxadiazol-2(3 <i>H</i> )-ones Using Carbonyldiimidazole

A convenient, metal-free one-pot synthesis has been developed to access 1,3,4-oxadiazol-2(3<i>H</i>)-ones using hydrazines, carboxylic acids, and 1,1'-carbonyldiimidazole (CDI) as an activating agent in the presence of triethylamine (TEA). This method can access the desired heterocycles in moderate to excellent yields in a one-pot transformation from commercially available starting materials, representing a significantly simpler path to access these compounds compared with existing tactics. The substrate scope investigation demonstrated that this method is broadly applicable and scalable.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-31
DOI
https://doi.org/10.1021/acs.joc.5c02625
Primary Topic
Structural and Chemical Analysis of Organic and Inorganic Compounds
Type
article
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article

One-Pot Method to Access 1,3,4-Oxadiazol-2(3 H )-ones Using Carbonyldiimidazole

Rakesh Sachdeva, Rajib Islam, Christopher D. Chouinard, Heidi M. Sabatini et al.
The Journal of Organic Chemistry
Structural and Chemical Analysis of Organic and Inorganic Compounds
article

One-Pot Method to Access 1,3,4-Oxadiazol-2(3 H )-ones Using Carbonyldiimidazole

Rakesh Sachdeva, Rajib Islam, Christopher D. Chouinard, Heidi M. Sabatini, Colin McMillen, Daniel C. Whitehead, Kaleb R. Marahrens
article en

Abstract

A convenient, metal-free one-pot synthesis has been developed to access 1,3,4-oxadiazol-2(3<i>H</i>)-ones using hydrazines, carboxylic acids, and 1,1'-carbonyldiimidazole (CDI) as an activating agent in the presence of triethylamine (TEA). This method can access the desired heterocycles in moderate to excellent yields in a one-pot transformation from commercially available starting materials, representing a significantly simpler path to access these compounds compared with existing tactics. The substrate scope investigation demonstrated that this method is broadly applicable and scalable.

The Journal of Organic ChemistryVol. 91(2)
Clemson University (US)
Openalex Percentile: Top 32%
Structural and Chemical Analysis of Organic and Inorganic Compounds
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