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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
6
|
pubmed:dateCreated |
1998-9-21
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pubmed:abstractText |
1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1-(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.
|
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
|
pubmed:chemical | |
pubmed:status |
MEDLINE
|
pubmed:month |
Jun
|
pubmed:issn |
0732-8311
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pubmed:author | |
pubmed:issnType |
Print
|
pubmed:volume |
17
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pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
1053-75
|
pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading | |
pubmed:year |
1998
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pubmed:articleTitle |
Heterocyclic nucleoside analogues by cycloaddition reactions of 1-vinylthymine with 1,3-dipoles.
|
pubmed:affiliation |
Chemistry Department, Heriot-Watt University, Riccarton, Edinburgh, UK.
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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