Source:http://linkedlifedata.com/resource/pubmed/id/19199666
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
4
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| pubmed:dateCreated |
2009-2-16
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| pubmed:abstractText |
Treating benzylcyanide with nitric oxide in basic methanol returns 3-oxo-4-phenyl-5-amino-1,2,3-oxadiazole (a 5-iminium-sydnone N-oxide), 5, in addition to the known 2-(hydroxyimino)-2-phenylacetonitrile, 6, and the bisdiazeniumdiolate imidate salt, 7. Conditions for the separation and purification of the new 1,2,3-oxadiazole 5 are described along with its theory, structure, spectroscopy, and reactivity which demonstrate the predominance of the amino tautomer over the N-hydroxide tautomer. New derivatives of 5 include a Schiff base, from the condensation with salicylaldehyde, 8, and a dimethylamino analogue of 5, from its reaction with methyliodide and NaH. As with other related 3-oxo-1,2,3-oxadiazoles 5 has pronounced acid/base stability. Theoretical calculations demonstrate that the only other prior sydnone N-oxides prepared were misformulated as the N-hydroxide imines and are better described as 3-oxo-5-amino-derivatives of 1,2,3-oxadiazoles.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Feb
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| pubmed:issn |
1520-6904
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| pubmed:author | |
| pubmed:issnType |
Electronic
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| pubmed:day |
20
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| pubmed:volume |
74
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
1621-6
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| pubmed:year |
2009
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| pubmed:articleTitle |
A new synthetic route to 3-oxo-4-amino-1,2,3-oxadiazole from the diazeniumdiolation of benzyl cyanide: stable sydnone iminium N-oxides.
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| pubmed:affiliation |
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 2K6, Quebec, Canada. scott.bohle@mcgill.ca
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| pubmed:publicationType |
Journal Article
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