A Concomitant Allylic Azide Rearrangement/Intramolecular Azide鈥揂lkyne Cycloaddition Sequence

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• 作者：Rakesh H. Vekariya ; Ruzhang Liu ; Jeffrey Aub茅
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：16
• 期：7
• 页码：1844-1847
• 全文大小：302K
• 年卷期：v.16,no.7(April 4, 2014)
• ISSN：1523-7052

文摘

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.