Copper-catalyzed cascade preparation of dihydropyrimidin-4-ones from N -(Prop-2-yn-1-yl)amides and azides

Jinjin Wang; Jing Wang; Ping Lu; Yanguang Wang

doi:10.1021/jo401094j

Copper-catalyzed cascade preparation of dihydropyrimidin-4-ones from N -(Prop-2-yn-1-yl)amides and azides

Jinjin Wang, Jing Wang, Ping Lu^*, Yanguang Wang

^*此作品的通讯作者

Zhejiang University

科研成果: 期刊稿件 › 文章 › 同行评审

31 引用（Scopus）

摘要

Dihydropyrimidin-4-ones were efficiently synthesized from copper catalyzed reaction between N-(prop-2-yn-1-yl)amides and sulfonylazides under mild conditions in moderate to excellent yields (up to 96% yields). The cascade process involves the copper-catalyzed alkyne-azide cycloaddition, the formation of ketenimine intermediate, the intramolecular nucleophilic addition of ketenimine, and subsequent rearrangement.

源语言	英语
页（从-至）	8816-8820
页数	5
期刊	Journal of Organic Chemistry
卷	78
期	17
DOI	https://doi.org/10.1021/jo401094j
出版状态	已出版 - 6 9月 2013
已对外发布	是

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abstract = "Dihydropyrimidin-4-ones were efficiently synthesized from copper catalyzed reaction between N-(prop-2-yn-1-yl)amides and sulfonylazides under mild conditions in moderate to excellent yields (up to 96% yields). The cascade process involves the copper-catalyzed alkyne-azide cycloaddition, the formation of ketenimine intermediate, the intramolecular nucleophilic addition of ketenimine, and subsequent rearrangement.",

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AU - Lu, Ping

AU - Wang, Yanguang

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N2 - Dihydropyrimidin-4-ones were efficiently synthesized from copper catalyzed reaction between N-(prop-2-yn-1-yl)amides and sulfonylazides under mild conditions in moderate to excellent yields (up to 96% yields). The cascade process involves the copper-catalyzed alkyne-azide cycloaddition, the formation of ketenimine intermediate, the intramolecular nucleophilic addition of ketenimine, and subsequent rearrangement.

AB - Dihydropyrimidin-4-ones were efficiently synthesized from copper catalyzed reaction between N-(prop-2-yn-1-yl)amides and sulfonylazides under mild conditions in moderate to excellent yields (up to 96% yields). The cascade process involves the copper-catalyzed alkyne-azide cycloaddition, the formation of ketenimine intermediate, the intramolecular nucleophilic addition of ketenimine, and subsequent rearrangement.

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Copper-catalyzed cascade preparation of dihydropyrimidin-4-ones from N -(Prop-2-yn-1-yl)amides and azides

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