Synthesis of Molsidomine and Mesocarb Analog via Mechanochemistry

Abstract

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.