Organocatalytic 1,3-Dipolar Cyclo­addition Reaction of β-Keto Amides with Azides - Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazole-4-carb­oxamides

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• 作者：Xiao Zhou ; Xianhong Xu ; Kun Liu ; Hua Gao ; Wei Wang and Wenjun Li
• 关键词：Click chemistry ; Azides ; Cycloaddition ; Enolates ; Nitrogen heterocycles
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：2016
• 期：10
• 页码：1886-1890
• 全文大小：991K
• ISSN：1099-0690

文摘

Organocatalytic [3+2] 1,3-dipolar cycloaddition reactions of β-keto amides with azides catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) have been developed. This strategy generates 1,4,5-trisubstituted 1,2,3-triazole-4-carboxamides in high yields and regioselectivities at room temperature. The reaction conditions have been optimized, and the scope of the β-keto amide and azide have been investigated. A mechanism for the reaction is also proposed.