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Iminosydnones (ImSyds) have renowned biological activities and attractive chemical properties for chemical biology. However, access to N6‐functionalized iminosydnones involves tricky and hazardous procedures. Thanks to an innovative mechanochemical strategy using 1,1'‐carbonyldiimidazole (CDI) as an activating agent, a straightforward synthesis of molsidomine and of a mesocarb analog, two bioactive iminosydnones, was achieved. The whole process, involving 4 linear steps, was carried out in the solid state by ball‐milling and with safe reagents, offering efficient and sustainable access to N‐carbonylated iminosydnones, in agreement with the principles of green chemistry. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

Synthetic mechanochemistry, the use of mechanical force produced by milling, grinding or extruding, as an activation technique, provides access to chemical entities of all kinds. This Review is focused on examples reported so far of known Active Pharmaceutical Ingredients (APIs), and effectively evaluated bioactive molecules, all prepared by mechanosynthesis. Three families of molecules are discussed: heterocyclic compounds, metal complexes and peptides. Advantages of the mechanochemistry approach are highlighted especially from a green chemistry and efficacy point of view. [ABSTRACT FROM AUTHOR]

Sydnones are mesioionic compounds studied for years for their versatile reactivity in substitution reactions, sydnone-alkyne or sydnone-alkene cycloaddition reactions. This perspective article focuses on the use of sydnones in coordination complexes, either through a metalation on one of the carbons of the sydnone ring, its modification to obtain polydentate ligands, or its use as a polar moiety that could influence the properties of the final complex. Such compounds are valuable either from a synthetic point of view or for their biological properties. [ABSTRACT FROM AUTHOR]

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation. [ABSTRACT FROM AUTHOR]