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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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Publication details

The article was received on 02 Jan 2019, accepted on 07 Feb 2019 and first published on 07 Feb 2019


Article type: Paper
DOI: 10.1039/C9OB00004F
Citation: Org. Biomol. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB00004F

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