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Sydnone is a mesoionic heterocyclic aromatic chemical compound. Recent computational studies have, however, shown Sydnone and other similar mesoionic compounds to be nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization." A sydnone imine in which the keto group of sydnone (=O) has been replaced with an imino (=NH) group can be found as a substructure in the stimulant drugs feprosidnine and mesocarb.
Contents
Discovery
Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride.
Examples
The reactinon between methyl 3-benzyl-sydnone-4-acetate and diphenylacetylene is described in Ex1 of GB 1387306 gives an analog of Bufezolac.
References
Sydnone Wikipedia(Text) CC BY-SA