Linked Life Data

19331356

Source:http://linkedlifedata.com/resource/pubmed/id/19331356

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
9
pubmed:dateCreated
2009-4-24
pubmed:abstractText
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2'-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HCl to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
May
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
1
pubmed:volume
74
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3286-92
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles.
pubmed:affiliation
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't