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

^*Corresponding author for this work

Zhejiang University

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8816-8820
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	78
Issue number	17
DOIs	https://doi.org/10.1021/jo401094j
Publication status	Published - 6 Sept 2013
Externally published	Yes

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

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 - Wang, Jinjin

AU - Wang, Jing

AU - Lu, Ping

AU - Wang, Yanguang

PY - 2013/9/6

Y1 - 2013/9/6

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.

UR - https://www.scopus.com/pages/publications/84883818826

U2 - 10.1021/jo401094j

DO - 10.1021/jo401094j

M3 - Article

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ER -

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

Abstract

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