Sydnone

Sydnone

Names
IUPAC name 2H-Oxadiazol-5-one
Other names 1,2,3-Oxadiazol-5(2H)-one
Identifiers
CAS Number	534-24-7
3D model (JSmol)	Interactive image
ChemSpider	65792731
PubChem CID	12443168
InChI InChI=1S/C2H2N2O2/c5-2-1-3-4-6-2/h1,4H Key: BIGWXAGEQONZGD-UHFFFAOYSA-N
SMILES C1=NNOC1=O
Properties
Chemical formula	C2H2N2O2
Molar mass	86.050 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 John Campbell Earl  [ de ] and Alan W. Mackney  [ Wikidata ] 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] : 130  [3] : 554}

Chemical structure

Sydnones have the following resonance structures.^{[ citation needed ]} The exocyclic oxygen atom (O6) has a significant negative charge. ^[3]

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 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. ^[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

• Chemical compounds with unusual names
• Montréalone
• Münchnone
• Sydnone imine

References

1. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) " sydnones ". doi : 10.1351/goldbook.S06207
2. Stewart, F. H. C. (1 April 1964). "The Chemistry of the Sydnones". Chemical Reviews. 64 (2): 129–147. doi:10.1021/cr60228a004.
3. Browne, Duncan L.; Harrity, Joseph P.A. (January 2010). "Recent developments in the chemistry of sydnones". Tetrahedron. 66 (3): 553–568. doi:10.1016/j.tet.2009.10.085.
4. Earl, J. Campbell; Mackney, Alan W. (1935). "204. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives". Journal of the Chemical Society (Resumed): 899. doi:10.1039/jr9350000899.
5. Simas, Alfredo (1998). "Are mesoionic compounds aromatic?". Canadian Journal of Chemistry. 76 (6): 869–872. doi:10.1139/v98-065.
6. Patel, Keshav C.; Patel, Himanshu D. (2011). "Synthesis and Biological Evaluation of Coumarinyl Sydnone Derivatives". e-Journal of Chemistry. 8 (1): 113–118. doi: 10.1155/2011/705856 . ISSN   0973-4945.

• 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.

External links

• IUPAC Goldbook entry
• Dictionary of Organic Compounds