rdf:type |
|
lifeskim:mentions |
umls-concept:C0030004,
umls-concept:C0035493,
umls-concept:C0038761,
umls-concept:C0039859,
umls-concept:C0054666,
umls-concept:C0175921,
umls-concept:C0178528,
umls-concept:C0220781,
umls-concept:C0260127,
umls-concept:C0449444,
umls-concept:C1280500,
umls-concept:C1883254
|
pubmed:issue |
1
|
pubmed:dateCreated |
2009-12-28
|
pubmed:abstractText |
Dirhodium tetraacetate catalyzed reaction of alpha-diazo-beta-keto-carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4-carboxylates and 4-phosphonates by carbene N-H insertion and cyclodehydration. In stark contrast, dirhodium tetrakis(heptafluorobutyramide) catalysis results in a dramatic change of regioselectivity to give oxazole-5-carboxylates and 5-phosphonates. Alpha-diazo-beta-ketosulfones behave similarly and give 5-sulfonyloxazoles upon dirhodium tetrakis(heptafluorobutyramide) catalyzed reaction with carboxamides. The analogous reactions of thiocarboxamides give the corresponding thiazole-5-carboxylates, -phosphonates, and -sulfones.
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Jan
|
pubmed:issn |
1520-6904
|
pubmed:author |
|
pubmed:issnType |
Electronic
|
pubmed:day |
1
|
pubmed:volume |
75
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
152-61
|
pubmed:meshHeading |
pubmed-meshheading:19954177-Carboxylic Acids,
pubmed-meshheading:19954177-Catalysis,
pubmed-meshheading:19954177-Magnetic Resonance Spectroscopy,
pubmed-meshheading:19954177-Methane,
pubmed-meshheading:19954177-Molecular Structure,
pubmed-meshheading:19954177-Oxazoles,
pubmed-meshheading:19954177-Phosphonic Acids,
pubmed-meshheading:19954177-Rhodium,
pubmed-meshheading:19954177-Stereoisomerism,
pubmed-meshheading:19954177-Structure-Activity Relationship,
pubmed-meshheading:19954177-Sulfones,
pubmed-meshheading:19954177-Thiazoles
|
pubmed:year |
2010
|
pubmed:articleTitle |
Rhodium carbene routes to oxazoles and thiazoles. Catalyst effects in the synthesis of oxazole and thiazole carboxylates, phosphonates, and sulfones.
|
pubmed:affiliation |
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|