Sydnone: Synthesis, reactivity and biological activities

Sydnones are among the most well-known mesoionic compounds. Since their synthesis in 1935 by Earl and Mecknay, numerous researches have shown that the chemical behavior, physical and biological properties of sydnones make them among the most useful compounds in organic chemistry. Sydnones undergo thermal 1,3-dipolar cycloaddition reaction with dipolarophiles (alkynes or alkenes) to give exclusively derivatives containing a pyrazole moiety exhibiting numerous applications such as pharmaceuticals and agrochemicals. However, the sydnone cycloaddition reaction with alkynes requires harsh conditions like high temperatures and long reaction times giving poor regioselectivity on the resulting products. To overcome these constraints, new reactions named CuSAC (Copper-Catalyzed Sydnone-Alkyne Cycloaddition) and SPSAC (Strain-Promoted Sydnone-Alkyne Cycloaddition) and have been developed, leading to pyrazoles with interesting constant kinetics.