• Source: Sydnone

Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position. Like other mesoionic compounds they are di-polar, possessing both positive and negative charges which are delocalized across the ring. 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." Sydnones are heterocyclic compounds named after the city of Sydney, Australia.
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.




Discovery


Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride. Later work showed that this could be applied fairly generally to the nitrosamines of N-substituted amino acids.




Chemical structure






Examples


Cefanone (Cephanone)
Ipramidil
3-Thiomorpholino-sydnonimine U.S. patent 4,332,801
The reaction between methyl 3-benzyl-sydnone-4-acetate and diphenylacetylene is described in Ex1 of GB 1387306 gives an analog of Bufezolac.
Synthesis and Biological Evaluation of Coumarinyl Sydnone Derivatives.




See also


Chemical compounds with unusual names
Montréalone
Münchnone
Sydnone imine




References



S. Wiechmann; T. Freese; M. H. H. Drafz; E. G. Hübner; J. C. Namyslo; M. Nieger; A. Schmidt (2014). "Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses". Chem. Commun. 50 (80): 11822–11824. doi:10.1039/C4CC05461J. PMID 25156208.
Claude V. Greco; Wayne H. Nyberg; C. C. Cheng (1962). "Synthesis of Sydnones and Sydnone Imines". Journal of Medicinal Chemistry. 5 (4): 861–865. doi:10.1021/jm01239a022. PMID 14056419.
Wilson Baker; W. D. Ollis (1957). "Meso-ionic compounds". Quarterly Reviews, Chemical Society. 11: 15–30. doi:10.1039/QR9571100015. S2CID 96888271.
Joseph Fugger; Jack M. Tien; I. Moyer Hunsberger (1955). "The Preparation of Substituted Hydrazines. I. Alkylhydrazines via Alkylsydnones". J. Am. Chem. Soc. 77 (7): 1843–1848. doi:10.1021/ja01612a039.
Jack M. Tien; I. Moyer Hunsberger (1955). "The Preparation of Substituted Hydrazines. II.1 3-Pyridylhydrazine via the Phototropic N-(3-Pyridyl)-sydnone". J. Am. Chem. Soc. 77 (24): 6604–6607. doi:10.1021/ja01629a052. 88, 178 (1961);
Jack M. Tien; I. Moyer Hunsberger (1961). "Sydnones. III. Preparation and Interconversion of Mercurated Derivatives of N-(3-Pyridyl)-sydnone1-3a". J. Am. Chem. Soc. 83 (1): 178–182. doi:10.1021/ja01462a035.
Alan R. Katritzky (1955). Chem. Ind.: 521. {{cite journal}}: Missing or empty |title= (help), ();
Alexander Lawson; D. H. Miles (1959). "Some new mesoionic compounds". J. Chem. Soc.: 2865–2871. doi:10.1039/JR9590002865.
J. Ogilvie; V. K. Miyamoto; Thomas C. Bruice (1961). "A Kinetic Study of the Reaction of a "Meso-ionic" Compound (Dehydrodithizone) with Haloacetates". J. Am. Chem. Soc. 83 (11): 2493–2495. doi:10.1021/ja01472a017.
LEMONT B. KIER, LAURETTA E. FOX, D. DHAWAN & I. W. WATERS (1962). "A New Class of Central Nervous System Stimulants". Nature. 195 (4843): 817–818. Bibcode:1962Natur.195..817K. doi:10.1038/195817a0. PMID 14455827. S2CID 1683698.{{cite journal}}: CS1 maint: multiple names: authors list (link)




External links


IUPAC Goldbook entry
Dictionary of Organic Compounds

Kata Kunci Pencarian:

• Sydnone
• Sydnone imine
• Mesocarb
• Mesoionic compounds
• Oxadiazole
• Montréalone
• Molsidomine
• Amfetaminil
• Controlled Drugs and Substances Act
• Münchnone