Sydnone
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Sydnones are mesoionic heterocyclic chemical compounds possessing a C5-oxygenated 1,2,3-oxadiazole core,[1][2][3] named after the city of Sydney, Australia. Like other mesoionic compounds they are dipolar, possessing both positive and negative charges which are delocalized across the ring.
Discovery
N-phenylsydnone was first prepared in 1935 by Template:Ill and Template:Ill by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride.[4] Later work showed that this could be applied fairly generally to the nitrosamines of N-substituted amino acids.[2]
The parent compound sydnone is not synthetically accessible and may not exist.[2]Template:Rp[3]Template:Rp
Chemical structure
Sydnones have the following resonance structures.Script error: No such module "Unsubst". The exocyclic oxygen atom (O6) has a significant negative charge.[3] File:Sydnone Resonance Structures.svg
Recent computational studies have indicated that sydnones and other similar mesoionic compounds are nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization."[5]
Examples
- Cefanone (Cephanone)
- Ipramidil
- 3-Thiomorpholino-sydnonimine U.S. patent 4332801
- The reaction between methyl 3-benzyl-sydnone-4-acetate and diphenylacetylene is described in Ex1 of <templatestyles src="Citation/styles.css"/>Template:Citation/make linkScript error: No such module "Check for unknown parameters". gives an analog of Bufezolac.
- Synthesis and Biological Evaluation of Coumarinyl Sydnone Derivatives.[6]
Related compounds
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.
See also
References
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- ↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "sydnones". Script error: No such module "CS1 identifiers".Script error: No such module "TemplatePar".
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External links
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