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.