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金催化的炔酰胺与 4,5-二氢-1,2,4-噁二唑的形式[3 + 2]环加成反应:功能化 4-氨基咪唑的合成。

Gold-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with 4,5-Dihydro-1,2,4-oxadiazoles: Synthesis of Functionalized 4-Aminoimidazoles.

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, People's Republic of China.

出版信息

Org Lett. 2017 Jun 16;19(12):3307-3310. doi: 10.1021/acs.orglett.7b01469. Epub 2017 May 26.

Abstract

A gold-catalyzed formal [3 + 2] cycloaddition of ynamides with 4,5-dihydro-1,2,4-oxadiazoles has been developed. The reaction provides a concise and regioselective access to highly functionalized 4-aminoimidazoles likely via the formation of an α-imino gold carbene intermediate followed by cyclization. 4,5-Dihydro-1,2,4-oxadiazole was found to act as an efficient N-iminonitrene equivalent in these reactions.

摘要

发展了一种金催化的炔酰胺与 4,5-二氢-1,2,4-噁二唑的[3+2]环加成反应。该反应通过形成α-亚氨基金卡宾中间体,随后环化,提供了一种简洁且区域选择性的方法来合成高官能化的 4-氨基咪唑。在这些反应中,发现 4,5-二氢-1,2,4-噁二唑是一种有效的 N-亚氨基氮烯等价物。

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