A Concomitant Allylic Azide Rearrangement/Intramolecular Azide–Alkyne Cycloaddition Sequence

An intramolecular Huisgen cycloaddition of an interconverting set of isomeric allylic azides with alkynes affords substituted triazoles in high yield. The stereoisomeric vinyl-substituted triazoloxazines formed depend on the rate of cycloaddition of the different allylic azide precursors when the re...

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Bibliographic Details
Published in:Organic letters 2014-04, Vol.16 (7), p.1844-1847
Main Authors: Vekariya, Rakesh H, Liu, Ruzhang, Aubé, Jeffrey
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Copper - chemistry
Cyclization
Cycloaddition Reaction
Iodides - chemistry
Letter
Molecular Structure
Stereoisomerism
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:An intramolecular Huisgen cycloaddition of an interconverting set of isomeric allylic azides with alkynes affords substituted triazoles in high yield. The stereoisomeric vinyl-substituted triazoloxazines formed depend on the rate of cycloaddition of the different allylic azide precursors when the reaction is carried out under thermal conditions. In contrast, dimerized macrocyclic products were obtained when the reaction was done using copper­(I)-catalyzed conditions, demonstrating the ability to control the reaction products through changing conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500011f