Synthesis of Novel Heterocyclic Structures via Reaction of Isocyanides with S-trans-Enones

The reaction of enone 1, bearing an internal nucleophilic moiety, i.e., furan or pyrrole (X = O, NR‘), with isocyanides is presented. The formation of products resulting from the reaction of the zwitterionic intermediate 2 with a second equivalent of isocyanide prior to cyclization to give 3, as wel...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 18; pp. 3975 - 3977
Main Authors Winkler, Jeffrey D, Asselin, Sylvie M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.08.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyanides - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Ketones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
REARRANGEMENT
NUCLEOPHILES
4+1 CYCLOADDITION
IMIDAZOLINES
CONSTRUCTION
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
VINYL ISOCYANATES
DERIVATIVES
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Summary:The reaction of enone 1, bearing an internal nucleophilic moiety, i.e., furan or pyrrole (X = O, NR‘), with isocyanides is presented. The formation of products resulting from the reaction of the zwitterionic intermediate 2 with a second equivalent of isocyanide prior to cyclization to give 3, as well as the direct formation of 4 from 2, is described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol061451c