| 词条 | Sydnone |
| 释义 |
|ImageFile=Sydnone parent compound.png |IUPACName=2~{H}-oxadiazol-5-one |OtherNames=1,2,3-Oxadiazol-5(2H)-one |Section1={{Chembox Identifiers | CASNo = 534-24-7 | PubChem=12443168 | ChemSpiderID = 65792731 | StdInChI=1S/C2H2N2O2/c5-2-1-3-4-6-2/h1,4H | StdInChIKey = BIGWXAGEQONZGD-UHFFFAOYSA-N | SMILES = C1=NNOC1=O }} |Section2={{Chembox Properties |C=2|H=2|N=2|O=2 }} }}Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position.[1][2][3] 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."[4] 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. DiscoverySydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso-N-phenylglycine with acetic anhydride.[5] Later work showed that this could be applied fairly generally to the nitrosamines of N-substituted amino acids.[2] Chemical structureExamples
See also
References1. ^{{GoldBookRef|title=sydnones|file = S05990}} 2. ^1 {{cite journal|last1=Stewart|first1=F. H. C.|title=The Chemistry of the Sydnones|journal=Chemical Reviews|date=1 April 1964|volume=64|issue=2|pages=129–147|doi=10.1021/cr60228a004}} 3. ^{{cite journal|last1=Browne|first1=Duncan L.|last2=Harrity|first2=Joseph P.A.|title=Recent developments in the chemistry of sydnones|journal=Tetrahedron|date=January 2010|volume=66|issue=3|pages=553–568|doi=10.1016/j.tet.2009.10.085}} 4. ^{{cite journal|last1=Simas|first1=Alfredo|title=Are mesoionic compounds aromatic?|journal=Canadian Journal of Chemistry|date=1998|volume=76|pages=869–872|doi=10.1139/v98-065}} 5. ^{{cite journal|last1=Earl|first1=J. Campbell|last2=Mackney|first2=Alan W.|title=204. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives|journal=Journal of the Chemical Society (Resumed)|date=1935|pages=899|doi=10.1039/jr9350000899}} 6. ^{{cite journal|last1=Patel|first1=Keshav C.|last2=Patel|first2=Himanshu D.|title=Synthesis and Biological Evaluation of Coumarinyl Sydnone Derivatives|journal=E-Journal of Chemistry|volume=8|issue=1|year=2011|pages=113–118|issn=0973-4945|doi=10.1155/2011/705856}}
| title = Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses. |author1=S. Wiechmann |author2=T. Freese |author3=M. H. H. Drafz |author4=E. G. Hübner |author5=J. C. Namyslo |author6=M. Nieger |author7=A. Schmidt | journal = Chem. Commun. | volume = 50 | issue = | pages = 11822–11824 | year = 2014 | url = | doi = 10.1039/C4CC05461J }}
| title = Synthesis of Sydnones and Sydnone Imines |author1=Claude V. Greco |author2=Wayne H. Nyberg |author3=C. C. Cheng |last-author-amp=yes | journal = Journal of Medicinal Chemistry | volume = 5 | issue = 4 | pages = 861–865 | year = 1962 | url = | doi = 10.1021/jm01239a022 }}
| title = Meso-ionic compounds |author1=Wilson Baker |author2=W. D. Ollis | journal = Quarterly Reviews, Chemical Society | volume = 11 | issue = | pages = 15–30 | year = 1957 | url = | doi = 10.1039/QR9571100015 }}
| title = The Preparation of Substituted Hydrazines. I. Alkylhydrazines via Alkylsydnones |author1=Joseph Fugger |author2=Jack M. Tien |author3=I. Moyer Hunsberger |last-author-amp=yes | journal = J. Am. Chem. Soc. | volume = 77 | issue = 7 | pages = 1843–1848 | year = 1955 | url = | doi = 10.1021/ja01612a039 }}
| title = The Preparation of Substituted Hydrazines. II.1 3-Pyridylhydrazine via the Phototropic N-(3-Pyridyl)-sydnone |author1=Jack M. Tien |author2=I. Moyer Hunsberger |lastauthoramp=yes | journal = J. Am. Chem. Soc. | volume = 77 | issue = 24 | pages = 6604–6607 | year = 1955 | url = | doi = 10.1021/ja01629a052 }} 88, 178 (1961);
| title = Sydnones. III. Preparation and Interconversion of Mercurated Derivatives of N-(3-Pyridyl)-sydnone1-3a |author1=Jack M. Tien |author2=I. Moyer Hunsberger |lastauthoramp=yes | journal = J. Am. Chem. Soc. | volume = 83 | issue = 1 | pages = 178–182 | year = 1961 | url = | doi = 10.1021/ja01462a035 }}
| title = | author = Alan R. Katritzky | journal = Chem. Ind. | volume = | issue = | pages = 521 | year = 1955 | url = | doi = }}, ();
| title = Some new mesoionic compounds |author1=Alexander Lawson |author2=D. H. Miles |lastauthoramp=yes | journal = J. Chem. Soc. | volume = | issue = | pages = 2865–2871 | year = 1959 | url = | doi = 10.1039/JR9590002865 }}
| title = A Kinetic Study of the Reaction of a "Meso-ionic" Compound (Dehydrodithizone) with Haloacetates |author1=J. Ogilvie |author2=V. K. Miyamoto |author3=Thomas C. Bruice | journal = J. Am. Chem. Soc. | volume = 83 | issue = 11 | pages = 2493–2495 | year = 1961 | url = | doi = 10.1021/ja01472a017 }}
| title = A New Class of Central Nervous System Stimulants | author = LEMONT B. KIER, LAURETTA E. FOX, D. DHAWAN & I. W. WATERS | journal = Nature | volume = 195 | issue = 4843 | pages = 817–818 | year = 1962 | url = | doi = 10.1038/195817a0 | pmid = 14455827 |bibcode = 1962Natur.195..817K }} External links
3 : Oxadiazoles|Simple aromatic rings|Lactones |
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