Volume 241, 2023

A mechanochemical approach to the synthesis of sydnones and derivatives

Abstract

Sydnones are heterocyclic compounds which display important biological activities, including their abilities to react in 1,3-dipolar additions for applications in the development of new prodrugs. Capitalizing on our preliminary work on the mechanosynthesis of sydnones, an extension of this work to two related families of molecules, diarylsydnones and iminosydnones is reported. A ball-milling approach towards the synthesis of diaryl sydnones was developed, a necessary step for the synthesis of potential sydnone-based ligands of metal complexes. A mechanochemistry-based synthesis of iminosydnones was optimized, including the preparation of active pharmaceutical ingredients (API) related to feprosidnine, linsidomine, mesocarb and molsidomine. This work demonstrated that the ball-milling procedures were efficient and time saving through avoiding purification steps, and reduced the use of organic solvents.

Graphical abstract: A mechanochemical approach to the synthesis of sydnones and derivatives

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
10 mai 2022
Accepted
04 jul 2022
First published
04 jul 2022
This article is Open Access
Creative Commons BY-NC license

Faraday Discuss., 2023,241, 114-127

A mechanochemical approach to the synthesis of sydnones and derivatives

N. Pétry, F. Luttringer, X. Bantreil and F. Lamaty, Faraday Discuss., 2023, 241, 114 DOI: 10.1039/D2FD00096B

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