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Issue 10, 2019
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Chemoselective syntheses of spirodihydrofuryl and spirocyclopropyl barbiturates via cascade reactions of barbiturate-based olefins and acetylacetone

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Abstract

The Michael addition initiated ring closure reaction of barbiturate-based olefins and acetylacetone with NBS has been explored. The efficient and chemoselective approach for the synthesis of barbiturate-fused spirocycles was established. Spirodihydrofuryl barbiturates and spirocyclopropyl barbiturates were synthesized selectively via cascade reactions under different basic conditions in moderate to excellent yields. The structure of 2-(4-chlorophenyl)-1,1-diacetyl-5,7-dimethyl-5,7-diazaspiro[2,5]octane-4,6,8-trione was confirmed by single crystal X-ray diffraction analysis.

Graphical abstract: Chemoselective syntheses of spirodihydrofuryl and spirocyclopropyl barbiturates via cascade reactions of barbiturate-based olefins and acetylacetone

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Article information


Submitted
02 Jan 2019
Accepted
07 Feb 2019
First published
07 Feb 2019

Org. Biomol. Chem., 2019,17, 2684-2690
Article type
Paper

Chemoselective syntheses of spirodihydrofuryl and spirocyclopropyl barbiturates via cascade reactions of barbiturate-based olefins and acetylacetone

X. Yan, P. Shao, X. Song, C. Zhang, C. Lu, S. Liu and Y. Li, Org. Biomol. Chem., 2019, 17, 2684
DOI: 10.1039/C9OB00004F

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