Linked Life Data

12005484

Source:http://linkedlifedata.com/resource/pubmed/id/12005484

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
2002-5-13
pubmed:abstractText
In this contribution, we constructed a library of butenolides with 77 members by parallel synthesis strategy on Merrifield resin. Sixteen 2,3-allenoic acids and 12 polymer-bound aryl iodides were combined to react with each other, and then the polymer-supported products were cleaved to release butenolide derivatives. The reactions with alkyl-substituted 2,3-allenoic acids in acetonitrile afforded the corresponding products in high yields and high purities, whereas those with aryl-substituted acids in acetonitrile failed. After some reaction conditions were screened, the solid-phase reactions with aryl-substituted 2,3-allenoic acids were realized in toluene, and the products are of good purities albeit in slightly low yields. In the benzyl ether linkage, a new cleavage model was found. By adding 6 equiv of acetyl bromide, we can get single (5-oxo-2,5-dihydrofuran-3-yl)benzyl bromide other than the corresponding benzyl acetate. To further increase the diversities, a dihydropyran (DHP) linker was introduced into our combinatorial synthesis of butenolides. By reversing the addition sequence of 2,3-allenoic acids and organic base, we realized the solid-phase cyclization reaction of polymer-bound aryl iodides with the THP linkage in moderate yields and good purities. Now the library of butenolides includes (5-oxo-2,5-dihydrofuran-3-yl)benzoic acids, -aryl acetates, -benzyl bromides, -benzyl alcohols, and -phenols, which are difficult to synthesize with conventional solution methods.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
1520-4766
pubmed:author
pubmed:issnType
Print
pubmed:volume
4
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
239-47
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:articleTitle
Palladium(0)-catalyzed coupling-cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. Solid-phase parallel synthesis of butenolides.
pubmed:affiliation
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't